[ CAS No. 615-13-4 ] {[proInfo.proName]}

Name: 615-13-4|1H-Inden-2(3H)-one|98%
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Quality Control of [ 615-13-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 615-13-4 ]

Product Details of [ 615-13-4 ]

CAS No. :	615-13-4	MDL No. :	MFCD00003792
Formula :	C₉H₈O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UMJJFEIKYGFCAT-UHFFFAOYSA-N
M.W :	132.16	Pubchem ID :	11983
Synonyms :

Calculated chemistry of [ 615-13-4 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	39.27
TPSA :	17.07 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.18 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.66
Log Po/w (XLOGP3) :	1.31
Log Po/w (WLOGP) :	1.35
Log Po/w (MLOGP) :	1.71
Log Po/w (SILICOS-IT) :	2.82
Consensus Log Po/w :	1.77

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.93
Solubility :	1.56 mg/ml ; 0.0118 mol/l
Class :	Very soluble
Log S (Ali) :	-1.27
Solubility :	7.11 mg/ml ; 0.0538 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.08
Solubility :	0.11 mg/ml ; 0.000832 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.28

Safety of [ 615-13-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 615-13-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 615-13-4 ]
Downstream synthetic route of [ 615-13-4 ]

[ 615-13-4 ] Synthesis Path-Upstream 1~8

1
[ 95-13-6 ]
[ 28272-96-0 ]
[ 83-33-0 ]
[ 615-13-4 ]

Reference： [1] Advanced Synthesis and Catalysis, 2004, vol. 346, # 2-3, p. 268 - 274

2
[ 7664-93-9 ]
[ 615-13-4 ]
[ 74-88-4 ]
[ 2177-47-1 ]

Yield	Reaction Conditions	Operation in experiment
30%	With magnesium In diethyl ether; dichloromethane; water; toluene	I.1. Synthesis of 2-methylindene 50 ml of diethylether was added to 2.5 grams of magnesium. A solution of 14.3 grams of methyliodide in 50 ml of diethylether was added for 1 hour while cooling with a water bath. The reaction mixture was then stirred at room temperature for 30 minutes. To this reaction mixture was added a solution of 13.2 grams of 2-indanone in 40 ml of diethylether, whereupon the mixture was stirred for 30 minutes. Hereafter, 100 ml of water was added. The organic layer was separated from the water layer. This water layer was washed twice with 50 ml of dichloromethane, whereafter the combined organic layers were dried on magnesium sulphate. On filtering off the drying agent, the filtrate was evaporated, leaving 14.0 grams of residue. This residue was dissolved in 100 ml of toluene, 4 drops of concentrated sulphuric acid were added and the resulting reaction mixture was refluxed for 30 minutes. After cooling down to room temperature, the mixture was washed once with 50 ml of water. The toluene was evaporated and the residue was vacuum distilled. Yield: 4.0 grams of 2-methylindene (30percent).

Reference： [1] Patent: US5646322, 1997, A,

3
[ 615-13-4 ]
[ 2177-47-1 ]

Reference： [1] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 11, p. 1453 - 1461
[2] Journal of the American Chemical Society, 1995, vol. 117, # 16, p. 4718 - 4719
[3] Journal of medicinal chemistry, 1969, vol. 12, # 3, p. 513 - 516

4
[ 75-16-1 ]
[ 615-13-4 ]
[ 2177-47-1 ]

Reference： [1] Journal of Organic Chemistry, 1980, vol. 45, # 26, p. 5247 - 5255
[2] Angewandte Chemie, 1992, vol. 104, # 10, p. 1373 - 1376

5
[ 917-54-4 ]
[ 615-13-4 ]
[ 2177-47-1 ]

Reference： [1] Journal of Organometallic Chemistry, 1996, vol. 519, # 1-2, p. 21 - 28

6
[ 615-13-4 ]
[ 17623-96-0 ]

Reference： [1] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 11, p. 1453 - 1461

7
[ 615-13-4 ]
[ 116530-60-0 ]

Yield	Reaction Conditions	Operation in experiment
49.5%	With nitric acid In chloroform at -20℃; for 1 h;	In the single neck 250ml flask was added 5.6g 2-indanone and 40mL chloroform. 13mL 95percent fuming nitric acid was measured. Both will be placed in a low temperature bath cooled to below -20°C. Cooled 2-indanone was slowly added cooled fuming nitric acid. The reaction system was stirred vigorously while adding dropwise for 40 minutes. After the addition was complete by TLC trace (developing solvent: chloroform:methanol = 100:1, product Rf = 0.64,2- indanone Rf = 0.79). The reaction was continued at -20°C for 20 minutes until reaction completion. With 60mL 10percent sodium hydroxide solution was mixed with ice water to quench the reaction. The reaction system presents two layers in a separating funnel. The upper layer was extracted with chloroform (3 × 30mL). The combined organic phases was washed with saturated brine until neutral. The organic solvent was evaporated by a rotary evaporator to give a yellow solid. Recrystallization using ethyl acetate and cyclohexane then cooling gave reddish-brown crystals. Filtration gave 3.8g 5-nitro-2-indanone, yield 49.5percent, mp 141-143°C.
49.5%	With nitric acid In chloroform at -20℃;	It has been reported that 2-indanone is able to convert to 5-nitro-2-indanone by fuming nitric acid with vigorous stirring at -20 °C according to modified published methodology [36] . To a cooled solution of 5.6 g 2-indanone in 40 mL chloroform was dropped slowly with 13 mL fuming nitric acid with vigorous stirring in 45 min at -20 °C. After the addition was completed, the mixture was then stirred further for 20 min, poured into a mixture of sodium hydroxide (6.5 g) in water and ice (ca. 50 mL), and then extracted twice with ethyl acetate. The combined extracts were washed with water until neutral, dried over magnesium sulfate, and evaporated in vacuum to yield yellow solid. Chloroform was used as the eluent in column chromatography. Finally, the crude product was recrystallized from ethyl acetate/hexane to give 3.7 g of product (49.5percent yield). m.p.:142-144 °C (lit [36] 141-143 °C).

Reference： [1] Journal of the American Chemical Society, 1997, vol. 119, # 52, p. 12722 - 12726
[2] Patent: CN105315204, 2016, A, . Location in patent: Paragraph 0028; 0032; 0033
[3] European Journal of Medicinal Chemistry, 2017, vol. 138, p. 738 - 747
[4] Chemische Berichte, 1899, vol. 32, p. 28,31

8
[ 7697-37-2 ]
[ 615-13-4 ]
[ 116530-60-0 ]

Reference： [1] Chemische Berichte, 1899, vol. 32, p. 28,31

[ 615-13-4 ] Synthesis Path-Downstream 1~87

1
[ 5400-80-6 ]
[ 615-13-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide nachfolgend Kochen mit Schwefelsaeure;

Reference： [1]Walters [Journal of the Society of Chemical Industry, 1927, vol. 46, p. 152 T][Chemisches Zentralblatt, 1927, vol. 98, # II, p. 69] Read; Hurst [Journal of the Chemical Society, 1922, vol. 121, p. 2554]

2
[ 100-63-0 ]
[ 615-13-4 ]
[ 7156-31-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sulfuric acid; toluene-4-sulfonic acid; In isopropyl alcohol; for 1h;Reflux;	To a 1000 mL 3-neck round bottom flask was added isopropyl alcohol (300 mL), And <strong>[615-13-4]2-indanone</strong> (30 g, 227 mmol),Phenylhydrazine (24.5 g, 227 mmol) and toluene sulfonic acid (1 g, 6.8 mmol)Respectively. The mixture was heated to reflux for 1 hour, cooled, and then added to isopropyl alcohol (50 mL) containing concentrated sulfuric acid (15 mL). The reaction mixture solution was heated to reflux for 1 hour.After cooling, 2.5%The solid was poured into an aqueous solution of sodium hydroxide and the precipitated solid was filtered under reduced pressure. The obtained solid was suspended in hexane, Filtered again and washed with hexane to obtain a yellow solid compound 3-A (41.9 g, yield: 90%).
75%	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; In ethyl acetate; at 110℃; for 0.25h;Microwave irradiation; Sealed vessel;	General procedure: T3P (50% in EtOAc) (0.55-0.68 mmol) was added to a mixture of hydrazine (59 mg, 0.55 mmol) and ketone/aldehyde (0.55 mmol) in a microwave vial. The reaction volume was then made up to 0.5 mL with EtOAc and the vessel was sealed under air. The mixture was heated under microwave irradiation (Biotage Initiator) at 100-150 C for 5-15 min. The solvent was evaporated under reduced pressure and the oily residue was purified by filtration through a plug of silica gel (eluent: isohexane/EtOAc, 8:2) to yield the desired indole or tetrahydrocarbazole. When the reaction was conducted on a 5 mmol scale the product (3a) was purified by precipitation from acetone/water.

Reference： [1]Patent: KR2017/131112,2017,A .Location in patent: Paragraph 0074-0077
[2]Tetrahedron Letters,2011,vol. 52,p. 4417 - 4420
[3]Journal of the Chemical Society,1922,vol. 121,p. 836

3
[ 95-13-6 ]
[ 615-13-4 ]

Yield	Reaction Conditions	Operation in experiment
97.1%		Step 1. Add 45 ml of glacial acetic acid, 27 ml of hydrogen peroxide and 3 g of AlCl3/SBA-15 supported catalyst to a 250 ml three-necked flask, and stir at 50 C;Step 2, was slowly added dropwise under incubation conditions 120ml 30ml of acetic anhydride and indene,Keep the reaction temperature not exceeding 55 C, complete the dropwise addition within 2 h, and react at 40 C for 12 h;Step 3, the solvent and water after the reaction are distilled off under reduced pressure, and the remaining liquid is cooled to -15 C for 2 h, the precipitated product is suction filtered, washed twice with distilled water, and dried under vacuum at 60 C for 8 h to obtain a white preliminary product;Step 4, take 10gThe initial product is added toIn a 250 ml round bottom flask,Add 50 ml of 10% dilute sulfuric acid aqueous solution, stir at 50 C for 2 h, cool to 5 C for 1 h, and filter to obtain pale yellow 2-indanone crude product;Step 5. The 2-indanone crude product is added to a 100 ml micro-sublimation apparatus, heated at 50 C, and the oil pump is sublimed under reduced pressure to obtain a white crystal 2-indanone.
78%		General procedure: To a solution of indene (1 eq.) in acetone (10 mL, for 1 mmol indene) were added ethyl acetate? (2 mL), water (2 mL) and solid NaHCO3 (12 eq.) and the reaction mixture was stirred for 10mm. To this was added solid Oxone (2 eq.) and contentswere stirred at room temperature for 15-18 h. After completion of the reaction, the excess acetone evaporated under reduced pressure and remaining reaction mixture portioned between water and ethyl acetate (20 mL each). The organic layer was separated and the aqueous layer extracted with ethyl acetate (2 x 20 mL). Combined organic layer was dried (Na2SO4) and concentrated under reduced pressure. Thecrude product was purified by silica gel column (ethyl acetate and pet ether as eluent) to afford the corresponding ketone.
78%		General procedure: To a solution of indene (1 eq.) in acetone (10 mL, for 1 mmol indene) were added ethyl acetate (2 mL), water (2 mL) and solid NaHCO3 (3 eq.) and the reaction mixture was stirred for 10 min. To this was added solid Oxone (0.5 eq.) and contents were stirred at room temperature for 15-18 h. After completion of the reaction, the excess acetone evaporated under reduced pressure and remaining reaction mixture portioned between water and ethyl acetate (20 mL each). The organic layer was separated and the aqueous layer extracted with ethyl acetate (2 x 20 mL). Combined organic layer was dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by silica gel column (ethyl acetate and pet ether as eluent) to afford the corresponding ketone

56.2%		A 250mL three-necked flask equipped with a thermometer and a pressure-equalizing dropping funnel was added 140mL 88% formic acid and 28mL 30% hydrogen peroxide, then heated with a water bath controlled to 35-40C. With a dropping funnel, exactly 26mL 90% indene was slowly dropped to the flask with stirring. After 2 hours the addition was complete. With a dropping funnel, 10ml of formic acid was added and stirring was continued at 35C for 20 minutes. This was followed by stirring at 25C for 7 hours. After completion of the reaction, excess acid was evaporated on a rotary evaporator (35mmHg / 35-40C ). The next step may be slightly heated before use to make liquefaction, easy to add liquid. In 500ml three-necked flask equipped with a distillation apparatus was added 300mL 7% sulfuric acid (V / V) then heated to boiling and slowly added to the remaining liquid. Water was added while steaming to ensure steam distillation. Water maintained at about 240-280mL. Distillate was a milky white liquid. Upon cooling white needle-like crystals precipitated. The reaction time required for the distillation is approximately 6 hours. The distillate was collected at a cooling temperature 10C under 12 hours then filtered to give white crystals. Vacuum dried at room temperature for 12 hours. 15g product, yield 56.2%, mp 57-58C.
56.2%		According to the reported methodology [35], 2-indanone wasknown that it can be obtained by oxidation of indene with formic acid and hydrogen peroxide. In a typical preparation process, 13 mL indene was added slowly in the mixture of 104 mL formic acid (88%) and 25 mL hydrogen peroxide (30%) at 35-40 C to give monoformate of 1,2-indanediol via ring-opening reaction after stirred for 6 h. Subsequently, hydrolysis of the monoformate gave 2-indanone by steam distilled in 150 mL7% (by volume) sulfuric acid. The cold distillate was filtered. The white crystals were dried further in a vacuum at room temperature for about 12 h to give 2-indanone 7.53 g (56.2% yield). m.p.: 57-59 C (lit [35] 57-58 C).
89%Spectr.	With [Ru(2,6-Cl2tpp)Cl2]; 2,6-dichloropyridine N-oxide; In chloroform-d1; at 60℃; for 10h;	Alkene substrate (0.1 mmol) and internal standard compound trimethylphenylsilicane(5 muL) were dissolved in CDCl3 (0.5 ml) in an NMR tube to record a 1H NMR. Then[RuIV(TDCPP)Cl2] (2.0 mol%) and Cl2pyNO (1.03 equiv) were added and kept themixture at 60 oC. The progress of the reaction was monitored by 1H NMR. Afterdetermination of the product yield by 1H NMR spectroscopy, the product ketone wasseparated by flash chromatography on silica gel.

Reference： [1]Molecular Crystals and Liquid Crystals,2008,vol. 484,p. 345/[711]-355/[721]
[2]Patent: CN109232211,2019,A .Location in patent: Paragraph 0008-0029
[3]Journal of the American Chemical Society,2016,vol. 138,p. 12037 - 12040
[4]Patent: WO2014/207766,2014,A1 .Location in patent: Page/Page column 30; 40
[5]Tetrahedron Letters,2015,vol. 56,p. 3868 - 3871
[6]Patent: CN105315204,2016,A .Location in patent: Paragraph 0028; 0030; 0031
[7]European Journal of Medicinal Chemistry,2017,vol. 138,p. 738 - 747
[8]Journal of the American Chemical Society,1985,vol. 107,p. 6975 - 6982
[9]Tetrahedron,1997,vol. 53,p. 7649 - 7670
[10]Organic Syntheses,1961,vol. 41,p. 53
[11]Angewandte Chemie,1959,vol. 71,p. 176,180,182
Angewandte Chemie,1962,vol. 74,p. 93
[12]Synthesis,1980,p. 621 - 623
[13]Journal of the American Chemical Society,1935,vol. 57,p. 2022,2025
[14]Journal of the American Chemical Society,1935,vol. 57,p. 2022,2025
[15]Molecular Crystals and Liquid Crystals,2010,vol. 522,p. 75 - 81
[16]Tetrahedron Letters,2014,vol. 55,p. 1736 - 1739
[17]Green Chemistry,2016,vol. 18,p. 3354 - 3359

4
[ 615-13-4 ]
[ 4385-35-7 ]

Reference： [1]Synthesis,1981,p. 818 - 820
[2]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 73 - 77
[3]Tetrahedron Asymmetry,1996,vol. 7,p. 417 - 420
[4]Organic and biomolecular chemistry,2003,vol. 1,p. 2120 - 2136
[5]Synthesis,1987,p. 497 - 498
[6]Synthesis,1991,p. 739 - 740
[7]Synthetic Communications,1989,vol. 19,p. 829 - 834
[8]Journal of the Chemical Society,1949,p. 1723
Journal of the Chemical Society,1958,p. 2038,2039

5
[ 615-13-4 ]
[ 24331-94-0 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 17019 - 17022,4
[2]Organic Letters,2020,vol. 22,p. 322 - 325
[3]Justus Liebigs Annalen der Chemie,1952,vol. 575,p. 197,214

6
[ 615-13-4 ]
[ 4254-29-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium tetrahydroborate; In ethanol; at 0℃;Inert atmosphere;	General procedure: Aldehyde (1 mmol) was dissolved in 10 ml ofmethanol(ethanol for ketones) and cooled to 0oC. NaBH4 (3 mmol) was then added inone portion and the reaction was allowed to stir until completion as indicatedby TLC (9:1 heptanes/ethyl acetate). The reaction was quenched with 0.1 N NaOH(10 ml) and extracted three times with ethyl actetate. The organic layer waswashed with brine and dried over Na2SO4. The solvent wasremoved under reduced pressure and the resulting yellow oil was subjected toflash chromatography.
98%	With methanol; sodium tetrahydroborate; at 25℃; for 1h;	To a solution of compound 76-1 (10 g, 0.076 mol) in MeOH (50 mL) was added sodium borohydride (NaBH4) (5.75 g, 0.15 mol) in portions at 25 C. and the reaction solution was stirred for 1 h. After TLC indicated the reaction was complete, the reaction was quenched with water (30 mL), and the aqueous phase was extracted with EtOAc (100 mL×3). Then the organic phases were combined, dried over anhydrous Na2SO4, filtered and evaporated to give compound 76-2 (white solid, 10 g, Yield: 98%). LCMS (ESI) m/z: 135 (M+1)
81.1%	With nickel-aluminum alloy; hydrogen; acetic acid; In methanol; at 20 - 60℃; under 3750.38 - 7500.75 Torr; for 5h;pH 4.4;Autoclave;	Wet sponge nickel catalyst (Nikko Rica Co., Ltd.)R-200) 3.5g in a beaker,After suspending in 150 g of water, leave it to stand and adjust the pH of the supernatant toWashing was repeated at room temperature until 8.7.After removing the supernatant, the suspension was suspended in methanol as a reaction solvent and allowed to stand, and the supernatant was removed and used for the reaction.In a 500 mL autoclave equipped with a thermometer and a stirrer, 200 g of methanol, washed sponge nickel catalyst,And 0.14 g of acetic acid was added and mixed.The pH of this suspension was 4.4. Purity to this suspensionAfter adding 20.0 g of 99.1% <strong>[615-13-4]2-indanone</strong>,The inside of the system was replaced with nitrogen at a pressure of 1.0 MPa three times at room temperature,Subsequently, it was replaced with 1.0 MPa of hydrogen three times.The system internal pressure is 0.5 to 1.0 MPa, the temperature is raised to 60 C.,A reduction reaction was performed, and after confirming that hydrogen absorption disappeared in 4 hours, stirring was further continued for 1 hour.The reaction rate of this reduction reaction was 99% or more.After cooling the reaction solution to room temperature, the catalyst was filtered off,The residue was washed with 10.0 g of methanol. after that,190 g of methanol was distilled off,170 g of water was added dropwise at room temperature. After stirring for 1 hour, the crystals are filtered,Drying gave 17.1 g of 2-indanol.The isolation yield is 81.1 mol%,The purity was 99.3%.The target contained in the filtrate is13.1 mol%, the combined yield with crystals isIt was 94.2 mol%.

With sodium tetrahydroborate; In methanol; at 20℃; for 0.166667h;

To a solution of [615-13-4]2-indanone 25 (1.0 g, 7.5 mmol, 1.0 equiv) in MeOH (150 mL) was added NaBH4 (500 mg, 12.2 mmol, 1.7 equiv) portionwise. The reaction was stirred 10 min then diluted with H2O (75 mL) and extracted with Et2O (2 * 100 mL). The organic layer was dried (MgSO4), filtered, and concentrated under reduced pressure to afford the crude product as a brown solid in quantitative yield. The product was utilized in the following step without further purification: Rf = 0.26 (20% EtOAc-Hexanes 1% Formic Acid); 1H NMR (600 MHz, CDCl3) delta 1.86 (br s, 1H), 2.91 (dd, J = 16.4, 2.9 Hz, 2H), 3.21 (dd, J = 16.4, 5.9 Hz, 2H), 4.68 (m, 1H), 7.18 (dd, J = 5.4, 3.6 Hz, 2H), 7.25 (dd, J = 5.4, 3.6 Hz, 1H).

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 108,p. 564 - 576
[2]Patent: US2017/313683,2017,A1 .Location in patent: Paragraph 1285-1286
[3]Angewandte Chemie - International Edition,2012,vol. 51,p. 12102 - 12106
Angew. Chem.,2012,p. 12077
[4]Chemical Communications,2013,vol. 49,p. 10151 - 10153
[5]RSC Advances,2014,vol. 4,p. 27955 - 27962
[6]Patent: JP5797108,2015,B2 .Location in patent: Paragraph 0028-0044
[7]European Journal of Organic Chemistry,2001,p. 2235 - 2243
[8]Tetrahedron,1982,vol. 38,p. 3769 - 3774
[9]Tetrahedron,1982,vol. 38,p. 3769 - 3774
[10]European Journal of Organic Chemistry,2018,vol. 2018,p. 1460 - 1464
[11]Chemical Communications,1997,p. 369 - 370
[12]Tetrahedron Letters,2009,vol. 50,p. 7314 - 7317
[13]Dalton Transactions,2017,vol. 46,p. 16412 - 16418
[14]Justus Liebigs Annalen der Chemie,1935,vol. 518,p. 155,173, 175
Justus Liebigs Annalen der Chemie,1938,vol. 533,p. 128,170
[15]Journal of the American Chemical Society,1965,vol. 87,p. 1297 - 1307
[16]Bulletin de la Societe Chimique de France,1968,p. 689 - 692
[17]Organic Mass Spectrometry,1982,vol. 17,p. 416 - 423
[18]Tetrahedron,2006,vol. 62,p. 8164 - 8168
[19]Chemical Communications,1997,p. 369 - 370
[20]Chemical Communications,2012,vol. 48,p. 4567 - 4569
[21]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 5605 - 5617
[22]Chemistry - A European Journal,2018,vol. 24,p. 17225 - 17229

7
[ 615-13-4 ]
[ 116530-60-0 ]

Yield	Reaction Conditions	Operation in experiment
49.5%	With nitric acid; In chloroform; at -20℃; for 1h;	In the single neck 250ml flask was added 5.6g 2-indanone and 40mL chloroform. 13mL 95% fuming nitric acid was measured. Both will be placed in a low temperature bath cooled to below -20C. Cooled 2-indanone was slowly added cooled fuming nitric acid. The reaction system was stirred vigorously while adding dropwise for 40 minutes. After the addition was complete by TLC trace (developing solvent: chloroform:methanol = 100:1, product Rf = 0.64,2- indanone Rf = 0.79). The reaction was continued at -20C for 20 minutes until reaction completion. With 60mL 10% sodium hydroxide solution was mixed with ice water to quench the reaction. The reaction system presents two layers in a separating funnel. The upper layer was extracted with chloroform (3 × 30mL). The combined organic phases was washed with saturated brine until neutral. The organic solvent was evaporated by a rotary evaporator to give a yellow solid. Recrystallization using ethyl acetate and cyclohexane then cooling gave reddish-brown crystals. Filtration gave 3.8g 5-nitro-2-indanone, yield 49.5%, mp 141-143C.
49.5%	With nitric acid; In chloroform; at -20℃;	It has been reported that 2-indanone is able to convert to 5-nitro-2-indanone by fuming nitric acid with vigorous stirring at -20 C according to modified published methodology [36] . To a cooled solution of 5.6 g 2-indanone in 40 mL chloroform was dropped slowly with 13 mL fuming nitric acid with vigorous stirring in 45 min at -20 C. After the addition was completed, the mixture was then stirred further for 20 min, poured into a mixture of sodium hydroxide (6.5 g) in water and ice (ca. 50 mL), and then extracted twice with ethyl acetate. The combined extracts were washed with water until neutral, dried over magnesium sulfate, and evaporated in vacuum to yield yellow solid. Chloroform was used as the eluent in column chromatography. Finally, the crude product was recrystallized from ethyl acetate/hexane to give 3.7 g of product (49.5% yield). m.p.:142-144 C (lit [36] 141-143 C).

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 12722 - 12726
[2]Patent: CN105315204,2016,A .Location in patent: Paragraph 0028; 0032; 0033
[3]European Journal of Medicinal Chemistry,2017,vol. 138,p. 738 - 747
[4]Chemische Berichte,1899,vol. 32,p. 28,31

8
[ 615-13-4 ]
[ 74-88-4 ]
[ 5689-12-3 ]

Yield	Reaction Conditions	Operation in experiment
66%	With potassium hydroxide; In dimethyl sulfoxide;	1a. 1,1,3,3-Tetramethyl<strong>[615-13-4]indan-2-one</strong> This was prepared as described by Langhals, E. and Langhals, H., Tetrahedron Lett., 31: 859-862, 1990. Potassium hydroxide (212 g, 3.8 mol) was pulverised and added to anhydrous DMSO (300 mL) in an oil bath preheated to 60 C. When the internal temperature reached 50 C. a solution of methyl iodide (93 mL, 213 g, 1.5 mol) and <strong>[615-13-4]2-indanone</strong> (25 g, 0.19 mol) in DMSO (50 mL) was added dropwise keeping the internal temperature between 50-55 C. After completion of the addition, the solution was stirred at 50 C. for 1 hour, cooled to room temperature, poured into ice-water (1.5 L) and extracted with ether (3500 mL). The combined organic phase was washed with water (2), dried over sodium sulfate, filtered and evaporated. The residue was sublimed at 3 mm Hg with a bath temperature of 70 C. to give the title compound (23 g, 66%). 1H NMR (300 MHz, CDCl3) delta7.24-7.33 (m, 4H), 1.35 (s, 12H).
45.1%	With potassium hydroxide; In dimethyl sulfoxide; at 50 - 60℃; for 1h;	Step 1: 1 , 1 ,3,3-tetramethyl- 1H-inden-2(3H)-one:Into a 3-necked round-bottomed flask equipped with a reflux condenser, mechanical stirrer, thermometer and dropping funnel was added DMSO (210 ml) and potassium hydroxide (1 12 g, 2 moles). The resulting suspension was heated at 50-55 . A solution of inden-2(3H)-one (13.2 g, 0.1 mol) and methyl iodide (50 ml, 0.8 mol) was added by portions so as to keep the temperature between 50 and 60 C (the heating was stopped after the first portion and cooling was applied when the temperature exceeded 60 C. Once the addition was completed, the resulting suspension was stirred for another 1 h. The excess methyl iodide was then distilled off. The suspension was then poured onto ice-water (500 ml) and extracted with hexane (2 times 150 ml). The combined hexane extracts were concentrated in vacuo to afford the title compound as a brown oil (8.5 g, 45.1 %).1H NMR (500 MHz, CDCI3): 7.14-7.08 (m, 4H), 1 .17 (s, 12H).

Reference： [1]Tetrahedron Letters,1990,vol. 31,p. 859 - 862
[2]Patent: US2003/203915,2003,A1
[3]Liebigs Annalen der Chemie,1980,p. 1207 - 1215
[4]Patent: WO2012/69852,2012,A1 .Location in patent: Page/Page column 84
[5]Journal of Organic Chemistry,1966,vol. 31,p. 1393 - 1402
[6]Chemische Berichte,1980,vol. 113,p. 2255 - 2277
[7]Tetrahedron,1997,vol. 53,p. 8137 - 8148
[8]Tetrahedron,2006,vol. 62,p. 8410 - 8418

9
[ 123-75-1 ]
[ 615-13-4 ]
[ 39157-79-4 ]

Yield	Reaction Conditions	Operation in experiment
48%	In toluene; at 70℃; for 24h;Molecular sieve 4A;	A mixture of 12.5 g (94.7 mmol) of indanone-2, 8.52 g (120 mmol) of pyrrolidine, 30 g of activated molecular sieves (4A), and 210 ml of toluene were stirred for 24 h at 7O0C. This mixture was cooled to room temperature, filtered through a glass frit (G2), and the precipitate (crushed molecular shieves) was washed with 3 x 30 ml of hexanes. The combined filtrate was evaporated to dryness, and the residue was recrystallized from 100 ml of hot hexanes. Crystals that precipitated at O0C were collected, washed with 2 x 10 ml of cold hexanes, and dried in vacuum. Yield 8.40 g (48%). <n="87"/>Anal. calc. for C13H15N: C, 84.28; H, 8.16. Found: C, 84.11; H, 8.21.1H NMR (CDCl3): delta 7.20 (d, J=7.3 Hz, IH, 7-H), 7.10 (t, J=7.3 Hz, IH, 6- H), 7.00 (d, J=7.3 Hz, IH, 4-H), 6.81 (t, J=7.3 Hz, IH, 5-H), 5.21 (br.s., IH, 3-H), 3.39 (s, 2H, 1-H), 3.25 (m, 4H, 2,2',5,5'-H in pyrrolidinyl), 1.97 (m, 4H, 3,3',4,4'- H in pyrrolidinyl).
	In toluene; for 2h;Inert atmosphere; Reflux; Dean-Stark;	Intermediate 4A Intermediate 4B 6'-Amino-r-methyl-r,3'-dihvdro-2H5H-spirorimidazolidine-4,2'-indene1-2,5-dione (Intermediate 4A) and 5'-Amino-r-methyl-r,3'-dihvdro-2H5H-spirorimidazolidine-4,2'- indenel-2,5-dione (Intermediate 4B) Step A. l-(lH-Inden-2-yl)pyrrolidine A mixture of <strong>[615-13-4]2-indanone</strong> (2.0 g, 15.1 mmol) and pyrrolidine (1.6 mL, 19.7 mmol) in anhydrous toluene (61 mL) was refluxed under nitrogen with azeotropic removal of water (Dean-Stark apparatus) for 2 h. The mixture was then cooled and concentrated to dryness in vacuo to give the title compound. MS:m/z = 186.2 (M + 1).

Reference： [1]Bioorganic and Medicinal Chemistry,2000,vol. 8,p. 1861 - 1869
[2]Recueil des Travaux Chimiques des Pays-Bas,1988,vol. 107,p. 549 - 562
[3]Patent: WO2007/70038,2007,A1 .Location in patent: Page/Page column 85-86
[4]Journal of Organic Chemistry,2011,vol. 76,p. 9015 - 9030
[5]Patent: WO2013/169567,2013,A1 .Location in patent: Page/Page column 64
[6]Patent: US2004/6226,2004,A1 .Location in patent: Page 7-8

10
[ 4254-29-9 ]
[ 615-13-4 ]

Yield	Reaction Conditions	Operation in experiment
78%	With [Cu6(SC5H4N)6]; potassium hydroxide; In toluene; at 70℃; for 24.0h;Glovebox; Inert atmosphere;	In the glove box, the 2 - yinyin mellow (1.0 mmol), [Cu6 (Pyt)6 ] (0.1 mmol), KOH (1.0 mmol) is added to the test tube with the magnetic coil in the has, then adding 2.0 ml dry toluene solvent. After the sealed reaction tube, is taken out of the glove box. Toward the nozzle leads into the small and stable and low production, stable air flow after such as, for 70 C reaction under 24 h; after the reaction, extracted with ethyl acetate (3 × 5 ml), the combined organic phase, dried with anhydrous sodium sulfate, filtered, concentrated filtrate for rotary evaporator, and then separating and purifying column law silica gel chromatography, to obtain the target product 2 - indenone (yield 78%).
68%	With pyridinium chlorochromate; In dichloromethane; at 20℃; for 4.0h;	A mixture of <strong>[4254-29-9]indan-2-ol</strong> (15, 99.7 mg, 0.74 mmol, 1 eq.), pyridinium chlorochromate (241.9 mg, 1.12 mmol, 1.5 eq.) and CH2Cl2 (3 mL) was vigorously stirred for 4 h at rt. A small amount of silica was added. Et2O (5 mL) was added and the reaction mixture was filtered under pressure. The residue was washed with Et2O. The filtrate was concentrated in vacuo. The crude product was purified by fc (d = 2 cm, l = 11 cm, v = 10 mL, cyclohexane:EtOAc 8:2, Rf = 0.11), yellow oil, yield 67.1 mg (68 %). C9H8O (132.2 g/mol). FT-IR (neat): nu (cm-1) = 2924 (C-H), 1743 (C=O), 740 and 648 (1,2-disubst. arom.). 1H NMR (400 MHz, CDCl3): delta (ppm) = 3.57 (s, 4H, 1-CH2, 3-CH2), 7.26 - 7.34 (m, 4H, Ar-H). 13C NMR (101 MHz, CD3OD): delta (ppm) = 44.2 (2C, C-1, C-3), 125.1 (2C, Cind), 127.5 (2C, Cind), 137.9 (2C, Cqind), 215.3 (1C, C=O). Exact Mass (APCI): m/z = 133.0654 (calcd. 133.0648 for C9H9O [M+H+]). Purity (HPLC, method 2) = 98.8 % (tR = 14.29 min).

Reference： [1]Synthetic Communications,2007,vol. 37,p. 4099 - 4103
[2]ChemCatChem,2017,vol. 9,p. 1113 - 1118
[3]Patent: CN106588957,2017,A .Location in patent: Paragraph 0043
[4]European Journal of Medicinal Chemistry,2020,vol. 190
[5]Journal of Medicinal Chemistry,2014,vol. 57,p. 8167 - 8179
[6]Journal of the American Chemical Society,1988,vol. 110,p. 8201 - 8206
[7]Tetrahedron Letters,2003,vol. 44,p. 9139 - 9142
[8]Dalton Transactions,2012,vol. 41,p. 10309 - 10316
[9]Journal of Molecular Catalysis A: Chemical,2016,vol. 425,p. 283 - 290

11
[ 490-63-1 ]
[ 615-13-4 ]
[ 78673-88-8 ]

Reference： [1]Australian Journal of Chemistry,1980,vol. 33,p. 2699 - 2715

12
[ 75-16-1 ]
[ 615-13-4 ]
[ 2177-47-1 ]

Reference： [1]Journal of Organic Chemistry,1980,vol. 45,p. 5247 - 5255
[2]Angewandte Chemie,1992,vol. 104,p. 1373 - 1376

13
[ 36600-66-5 ]
[ 615-13-4 ]
[ 136282-05-8 ]
[ 136282-19-4 ]

Reference： [1]Tetrahedron,1991,vol. 47,p. 4383 - 4408

14
[ 5326-84-1 ]
[ 615-13-4 ]
JPC 1-60-36 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium cyanoborohydride In methanol for 20h; Ambient temperature;

Reference： [1]Cannon, Joseph G.; Perez, Julio A.; Pease, Jonathan P; Long, John Paul; Flynn, Jan R.; et al. [Journal of Medicinal Chemistry, 1980, vol. 23, # 7, p. 745 - 749]

15
[ 6287-40-7 ]
[ 615-13-4 ]
N,N-dibutylindan [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1980,vol. 23,p. 745 - 749

16
[ 615-13-4 ]
[ 694-87-1 ]

Reference： [1]Tetrahedron Letters,1982,vol. 23,p. 3665 - 3668

17
[ 615-13-4 ]
[ 141120-17-4 ]

Yield	Reaction Conditions	Operation in experiment
	Yield given. Multistep reaction;

Reference： [1]Zon, Jerzy; Amrhein, Nikolaus [Liebigs Annalen der Chemie, 1992, # 6, p. 625 - 628]

18
[ 107-21-1 ]
[ 615-13-4 ]
[ 183-24-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With toluene-4-sulfonic acid; orthoformic acid triethyl ester; at 20℃; for 3h;	To a solution of <strong>[615-13-4]2-indanone</strong> (2 g, 15.2 mmol) in ethylene glycol (10 mL) was added triethylorthoformate (5 mL) and a crystal of TsOH. The reaction was stirred at room temperature for 3 h, and the solvent removed in vacuo. The residue was purified by flash column chromatography on silica gel (eluant: pet ether:ethyl acetate, 5:1) to yield the dioxane, (2.4 g, 90%), a colourless oil with the following physical properties: IR (film) numax/cm-1 2955, 2885, 1403, 1331, 1292, 1226, 1104, 1030 cm-1; 1H NMR (CDCl3, 400 Hz) deltaH 3.27 (4H, s, 2× CH2), 4.06 (4H, s, 2× OCH2), 7.23-7.28 (4H, m, 4× Ar-CH); 13C NMR deltaC 42.84 (2× CH2), 64.07 (2× OCH2), 117.11 (OCO), 124.14 (2× Ar-CH), 126.25 (2× Ar-CH), 139.45 (2× Ar-C); MS, m/z, (RI) 177 (M+1, 28), 176 (M+, 100), 117 (12), 104 (42).
85%	With toluene-4-sulfonic acid; In benzene; for 6h;Heating / reflux;	Indan-2-one (1.0 g, 7.6 mmol), ethylene glycol (0.43 mL, 7.6 mmol), and paratoluene sulphonic acid were refluxed in benzene (40 ml) using a Dean-Stark trap for 6 hours. The mixture was allowed to cool and was then diluted with ethyl acetate (100 mL) and washed with saturated sodium hydrogen carbonate solution (60 mL). The organic layer was separated off, and the aqueous layer was extracted further with ethyl acetate (2?50 mL). The combined organic fractions were washed with brine, dried (MgSO4), and the solvent was evaporated under reduced pressure. The residue was chromatographed (SiO2, heptane/ethyl acetate, 97:3) to give the acetal 1 (1.14 g, 85%) as a colorless oil; Rf(heptane/ethyl acetate, 8:2) 0.36; ?max(film)/cm?1 1483, 1331, 1291, 1105; ?H (400 MHz; CDCl3): 7.19-7.14 (4H, m, Ph), 4.02 (4H, s, 2?CH2CO2), 3.18 (4H, s, 2?CH2O).

Reference： [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 1545 - 1554
[2]Patent: US6689906,2004,B1 .Location in patent: Page column 18-19
[3]Journal of the Chemical Society. Perkin transactions I,1995,p. 2077 - 2078
[4]Beilstein Journal of Organic Chemistry,2013,vol. 9,p. 1668 - 1676

19
[ 7321-55-3 ]
[ 4647-42-1 ]
[ 615-13-4 ]
[ CAS Unavailable ]
[ 175166-51-5 ]

Yield	Reaction Conditions	Operation in experiment
30%	With trifluorormethanesulfonic acid In dichloromethane -40 deg C to room t.; Yield given;
30%	With trifluorormethanesulfonic acid In dichloromethane -40 deg C to room t.; Yields of byproduct given;

Reference： [1]Davies, Ian W.; Senanayake, Chris H.; Larsen, Robert D.; Verhoeven, Thomas R.; Reider, Paul J. [Tetrahedron Letters, 1996, vol. 37, # 6, p. 813 - 814]
[2]Davies, Ian W.; Senanayake, Chris H.; Larsen, Robert D.; Verhoeven, Thomas R.; Reider, Paul J. [Tetrahedron Letters, 1996, vol. 37, # 6, p. 813 - 814]

20
[ 4370-02-9 ]
[ 109-77-3 ]
[ 615-13-4 ]
(3aS,8aR)-(8,8a-Dihydro-3aH-indeno[1,2-d]oxazol-2-yl)-acetonitrile [ No CAS ]
[ 175166-49-1 ]

Reference： [1]Tetrahedron Letters,1996,vol. 37,p. 813 - 814
[2]Tetrahedron Letters,1996,vol. 37,p. 813 - 814
[3]Tetrahedron Letters,1996,vol. 37,p. 813 - 814

21
[ 609-40-5 ]
[ 95-13-6 ]
[ 16021-01-5 ]
[ 63440-60-8 ]
[ 615-13-4 ]
[ 150994-10-8 ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 14253 - 14272

22
[ 917-54-4 ]
[ 615-13-4 ]
[ 2177-47-1 ]

Reference： [1]Journal of Organometallic Chemistry,1996,vol. 519,p. 21 - 28

23
[ 18162-48-6 ]
[ 615-13-4 ]
[ 176377-30-3 ]

Yield	Reaction Conditions	Operation in experiment
89.6%	With 1H-imidazole; In DMF (N,N-dimethyl-formamide); at 20℃;	A solution of tert-butyldimethylchlorosilane (248.69 g, 1.65 mol) and imidazole (112.33 g, 1.65 mol) in DMF (900 mL) was reacted with <strong>[615-13-4]2-indanone</strong> (198.24 g, 1.50 mol) and then stirred overnight at room temperature. The reaction mixture was treated with water (800 mL) and extracted with diethyl ether (3 × 400 mL). The combined organic phases were washed with water (2 × 400 mL) and dried over sodium sulfate. The solvents were removed under reduced pressure to leave an orange oil. Distillation under reduced pressure gave 331.2 g (89.6%) of the title compound as a yellow oil (bp 105-107 C/0.1 mbar). 1H NMR (CDCl3, delta): 7.19-7.07 (m, 3H); 6.97 (td, 3J = 7.3 Hz, 4J = 1.4 Hz, 1H); 5.72 (dd, 4J = 1.9 Hz, 1.1 Hz, 1H); 3.24 (dd, 4J = 1.7 Hz, 1.1 Hz, 2H); 0.96 (s, 9H); 0.23 (s, 6H). 13C NMR (CDCl3, delta): 162.44; 145.14; 136.53; 126.44; 123.01; 122.39; 118.92; 106.58; 39.46; 25.59; 18.14; -4.68.

Reference： [1]Patent: EP880534,2003,B1 .Location in patent: Page/Page column 5; 9; 23
[2]Chemical Communications,1997,p. 1169 - 1170

24
[ 7677-24-9 ]
[ 615-13-4 ]
[ 55589-22-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With copper(II) bis(trifluoromethanesulfonate); In dichloromethane; at 20℃;	General procedure: A solution of a <strong>[615-13-4]2-indanone</strong> intermediate of formula (XIV), trimethylsilyl cyanide (2.6 eq) and copper(II) trifluoromethanesulfonate (0.01 eq) in dichloromethane (0.5-1.0 M) is stirred at room temperature for 15-24 h. The reaction mixture is concentrated to dryness to give a trimethylsilyl cyanohydrin intermediate of formula (XVI). The crude compound of formula (XVI) is partitioned between an organic solvent such as dichloromethane and water. The layers are separated. The aqueous layer is extracted with one or two portions of organic solvent. The combined organic layers are washed with one portion of brine, dried over anhydrous sodium sulfate, filtered and concentrated to dryness to give an intermediate of formula (XVI). During the work-up the trimethylsilyl group of the resulting trimethylsilyl cyanohydrin may be partially or completely cleaved to give a cyanohydrin intermediate of formula (XV).

Reference： [1]Patent: WO2015/91411,2015,A1 .Location in patent: Page/Page column 85; 86
[2]Synlett,1999,p. 315 - 316
[3]Organic Process Research and Development,2003,vol. 7,p. 155 - 160

25
[ 7697-37-2 ]
[ 615-13-4 ]
[ 116530-60-0 ]

Reference： [1]Chemische Berichte,1899,vol. 32,p. 28,31

26
[ 95-13-6 ]
oxygen [ No CAS ]
[ 768-22-9 ]
[ 495-78-3 ]
[ 4370-02-9 ]
[ 615-13-4 ]

Reference： [1]Chemische Berichte,1951,vol. 84,p. 122,123

27
[ 5400-80-6 ]
[ 615-13-4 ]

Yield	Reaction Conditions	Operation in experiment
	nachfolgend Kochen mit verd. Schwefelsaeure;

28
[ 5446-02-6 ]
[ 615-13-4 ]
9-methoxy-11H-10-oxa-benzo[b]fluoren-5-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%	Stage #1: 4-methoxymethylsalicylate; 2-indanone In tetrahydrofuran at 0℃; for 2h; Stage #2: With hydrogenchloride In tetrahydrofuran; water for 1h; Heating;

Reference： [1]Townsend, Jessica D.; Williams, Angela R.; Angel, April J.; Finefrock, Anne E.; Beam, Charles F. [Synthetic Communications, 2000, vol. 30, # 4, p. 689 - 699]

29
[ 22717-57-3 ]
[ 615-13-4 ]
7-methyl-11H-10-oxa-benzo[b]fluoren-5-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	Stage #1: methyl 6-hydroxy-m-toluate; 2-indanone In tetrahydrofuran at 0℃; for 2h; Stage #2: With hydrogenchloride In tetrahydrofuran; water for 1h; Heating;

Reference： [1]Townsend, Jessica D.; Williams, Angela R.; Angel, April J.; Finefrock, Anne E.; Beam, Charles F. [Synthetic Communications, 2000, vol. 30, # 4, p. 689 - 699]

30
[ 6342-70-7 ]
[ 615-13-4 ]
8-methoxy-11H-10-oxa-benzo[b]fluoren-5-one [ No CAS ]

Reference： [1]Synthetic Communications,2000,vol. 30,p. 689 - 699

31
[ 4068-75-1 ]
[ 615-13-4 ]
7-iodo-11H-10-oxa-benzo[b]fluoren-5-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24%	Stage #1: methyl 5-iodosalicylate; 2-indanone In tetrahydrofuran at 0℃; for 2h; Stage #2: With hydrogenchloride In tetrahydrofuran; water for 1h; Heating;

Reference： [1]Townsend, Jessica D.; Williams, Angela R.; Angel, April J.; Finefrock, Anne E.; Beam, Charles F. [Synthetic Communications, 2000, vol. 30, # 4, p. 689 - 699]

32
[ 18328-90-0 ]
[ 615-13-4 ]
2-[ethyl(2-methallyl)amino]indene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With 3 A molecular sieve In toluene at 70℃; for 24h;

Reference： [1]Faure, Jean-Luc; Erker, Gerhard; Froehlich, Roland; Bergander, Klaus [European Journal of Inorganic Chemistry, 2000, # 12, p. 2603 - 2606]

33
[ 615-13-4 ]
methyl-Mg-halide [ No CAS ]
[ 2177-47-1 ]

Reference： [1]Journal of Organometallic Chemistry,2000,vol. 616,p. 112 - 127

34
[ 35737-10-1 ]
[ 69342-47-8 ]
[ 615-13-4 ]
[ 164470-64-8 ]
3-{4-[1-(2,3-Dihydro-1H-inden-2-yl)-3-(4-butylphenyl)ureidomethyl]benzoylamino)propionic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 113 - 128

35
[ 35737-10-1 ]
[ 24032-84-6 ]
[ 615-13-4 ]
[ 164470-64-8 ]
3-{4-[1-indan-2-yl-3-(4-trifluoromethylsulfanyl-phenyl)-ureidomethyl]-benzoylamino}-propionic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 113 - 128

36
[ 615-13-4 ]
MeMgX [ No CAS ]
[ 2177-47-1 ]

Reference： [1]Tetrahedron,2006,vol. 62,p. 11477 - 11482

37
[ 615-13-4 ]
[ 92013-12-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: Mg / diethyl ether / 2 h 1.2: diethyl ether 2.1: p-toluenesulfonic acid / toluene / Heating
	Multi-step reaction with 2 steps 1: 1) LaCl₃ / 1) THF, 1 h, 0 deg C, 2) THF, 2 h 2: p-TsOH*H₂O / toluene / 2 h / Heating

Reference： [1]Schmidt, Roland; Alt, Helmut G. [Journal of Organometallic Chemistry, 2001, vol. 621, # 1-2, p. 304 - 309]
[2]Lee, Gong Yeal; Xue, Ming; Kang, Myoung Soon; Kwon, Oh Chul; Yoon, Jin-San; Lee, Yoo-Su; Kim, Hoon Sik; Lee, Hyunjoo; Lee, Ik-Mo [Journal of Organometallic Chemistry, 1998, vol. 558, # 1-2, p. 11 - 18]

38
[ 615-13-4 ]
[ 2177-47-1 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1999,p. 1453 - 1461
[2]Journal of the American Chemical Society,1995,vol. 117,p. 4718 - 4719
[3]Journal of medicinal chemistry,1969,vol. 12,p. 513 - 516

39
[ 615-13-4 ]
[ 83094-62-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 12 percent / toluene dioxygenase from Pseudomonas putida UV₄ / 24 h 2: 61 percent / SOCl₂; pyridine / CHCl₃ / 3 h / Heating

Reference： [1]Bowers, Nigel I.; Boyd, Derek R.; Sharma, Narain D.; Goodrich, Peter A.; Groocock, Melanie R.; Blacker, A. John; Goode, Paul; Dalton, Howard [Journal of the Chemical Society. Perkin transactions I, 1999, # 11, p. 1453 - 1461]

40
[ 615-13-4 ]
[ 17623-96-0 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1999,p. 1453 - 1461

41
[ 615-13-4 ]
[ 71066-00-7 ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 11807 - 11816
[2]Patent: WO2012/119941,2012,A1

42
[ 615-13-4 ]
[ 33982-85-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 2: 90 percent / (n-Bu)3PO, LiClO_4.3H₂O / toluene / 2.5 h / Heating

Reference： [1]Satoh, Tsuyoshi; Itoh, Masayuki; Ohara, Teruhiko; Yamakawa, Koji [Bulletin of the Chemical Society of Japan, 1987, vol. 60, p. 1839 - 1846]

43
[ 615-13-4 ]
colloidal platinum [ No CAS ]
[ 2177-47-1 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1981,vol. 323,p. 607 - 615

44
[ 615-13-4 ]
aqueous methanolic NaOH-solution [ No CAS ]
[ 2177-47-1 ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 281 - 283

45
[ 613-73-0 ]
[ 615-13-4 ]

Reference： [1]Journal of the Chemical Society,1922,vol. 121,p. 1570

46
[ 867-13-0 ]
[ 615-13-4 ]
[ 143356-09-6 ]

Yield	Reaction Conditions	Operation in experiment
87%	With sodium hydride; In tetrahydrofuran; at 0 - 20℃; for 3.25h;	Triethylphosphonoacetate (5.5 mL, 27.8 mmol) was slowly added (over 15 minutes) to a suspension of sodium hydride (1.06 g, 26.6 mmol) in THF (60 mL) at 0C under nitrogen. Gas was evolved and the solution went clear. Next, <strong>[615-13-4]2-indanone</strong> (1) (335 g, 25.3 mmol in THF (10 mL + 5 mL) was added, and the solution was allowed to warm to room temperature with stirring over 3 hours, after which the reaction was diluted with water (150 mL) and extracted with ether (2 200 mL), then dried (MgSO4). The organic phase was concentrated in vacuo. Column chromatography (40% ethyl acetate in heptane) gave 4.45 g (87%) of the product as an oil.1H NMR (CDCl3) ? = 7.40 (4H, m), 7.31 (1H, d, J 7.6), 7.25 (1H, t, J 7.6), 7.15 (1H, t, J 7.4), 6.7 (1H, br s), 4.18 (2H, q, J 7.1), 3.52 (2H, s), 3.45 (2H, s), 3.45 (2H, s), 1.28 (3H, t, J 7.2). I.R (thin film) (cm-1) ? = 2981, 1782, 1734, 1613, 1461, 1369, 1174, 1029, 753.

Reference： [1]Patent: EP1180094,2004,B1 .Location in patent: Page 15

47
[ 17113-33-6 ]
[ 615-13-4 ]
[ 380910-89-4 ]

Yield	Reaction Conditions	Operation in experiment
31%		In a 1000-ml glass reaction vessel, 33 g (0.23 mol) of <strong>[17113-33-6]2-phenylfuran</strong> and 300 ml of THF were placed and cooled to -70 C. in a dry ice-methanol bath. To the cooled mixture, 147 ml (0.23 mol) of a 1.56 mol/L n-butyllithium-hexane solution was added dropwise. After the dropwise addition, the mixture was allowed to warm to room temperature while stirring for 4 hours. The mixture was again cooled to -70 C. in a dry ice-methanol bath and 100 ml of a THF solution containing 30 g (0.23 mol) of 2-indanone was added dropwise. After the dropwise addition, the mixture was allowed to gradually warm to room temperature while stirring for 16 hours. The reaction solution was cooled to -20 C. in the dry ice-methanol bath, and 100 ml of 4N-hydrochloric acid was added dropwise. The reaction solution was transferred to a separation funnel and washed with a saline solution until neutrality. Sodium sulfate anhydride was added to the reaction solution, which was allowed to stand overnight and dried. The sodium sulfate anhydride was filtered off and the solvent was distilled off under reduced pressure. 600 ml of toluene and 0.5 g (2.6 mmol) of p-toluene sulfonic acid were added, and the solution was heated to reflux for 1 hour. The reaction solution was transferred to a separation funnel and washed with a saline solution until neutrality. Sodium sulfate anhydride was added to the solution, which was allowed to stand overnight and dried. The sodium sulfate anhydride was filtered off and the solvent was distilled off under reduced pressure. The residue was purified with a silica gel column to obtain 19 g (yield 31%) of 2-(2-(5-phenyl)-furyl)-indene as colorless needle crystals. The structure was confirmed by NMR.

Reference： [1]Patent: US6846943,2005,B2 .Location in patent: Page/Page column 39-40

48
[ 7664-93-9 ]
[ 615-13-4 ]
[ 74-88-4 ]
[ 2177-47-1 ]

Yield	Reaction Conditions	Operation in experiment
30%	With magnesium; In diethyl ether; dichloromethane; water; toluene;	I.1. Synthesis of 2-methylindene 50 ml of diethylether was added to 2.5 grams of magnesium. A solution of 14.3 grams of methyliodide in 50 ml of diethylether was added for 1 hour while cooling with a water bath. The reaction mixture was then stirred at room temperature for 30 minutes. To this reaction mixture was added a solution of 13.2 grams of 2-indanone in 40 ml of diethylether, whereupon the mixture was stirred for 30 minutes. Hereafter, 100 ml of water was added. The organic layer was separated from the water layer. This water layer was washed twice with 50 ml of dichloromethane, whereafter the combined organic layers were dried on magnesium sulphate. On filtering off the drying agent, the filtrate was evaporated, leaving 14.0 grams of residue. This residue was dissolved in 100 ml of toluene, 4 drops of concentrated sulphuric acid were added and the resulting reaction mixture was refluxed for 30 minutes. After cooling down to room temperature, the mixture was washed once with 50 ml of water. The toluene was evaporated and the residue was vacuum distilled. Yield: 4.0 grams of 2-methylindene (30%).

Reference： [1]Patent: US5646322,1997,A

49
[ 1020635-78-2 ]
[ 615-13-4 ]
[ 1020635-22-6 ]

Yield	Reaction Conditions	Operation in experiment
78%		Ethyl 6-(2,3-dihydro-lH-inden-2-ylamino)-l-ethyl-l,4-dihydro-4-oxo-l,8- naphthyridine-3-carboxylateA stirred solution of the naphthyridine (0.1 mmol), sodium sulfate (1.0 mmol), 2- indanone (0.15 mmol) and AcOH (7.5 ml) in dichloroethane (30 ml) under a nitrogen atmosphere was allowed to mature for 15 mins at room temperature. Sodium triacetoxyborohydride (0.15 mmol) was then added in one portion and the solution was allowed to stir for 4 h at rt (the reaction was monitored by TLC). A second addition of sodium sulfate (1.0 mmol), <strong>[615-13-4]2-indanone</strong> (0.15 mmol) and sodium triacetoxyborohydride (0.15 mmol) and stirring overnight was required to drive the reaction to completion. The reaction mixture was quenched with 10% sodium hydrogen carbonate solution and dichloromethane added to dilute the solution. The organic layer was separated from the aqueous layer and the organic layer dried(MgSO4). The organic layer was concentrated in vacuo and the resulting residue subjected to silica column chromatography, gradient-eluting with 100 % dichloromethane and then 1 % MeOH/dichloromethane to give an oily residue. The residue was triturated using diethyl ether and the solid was filtered off at the pump to afford a pale yellow solid (78 %).ESIMS: M+l: found 378; expected 378;1H NMR (300 MHz, CDCl3) ? 8.64 (IH, s, H-2), 8.30 (IH, d,H-5), 7.55 (IH, d, H-7), 7.23-7.10 (4H, m, 3xArH), 6.69 (IH, d, NH), 4.41 (3H, q,OCH2), 4.38-4.23 (IH, m, NCH), 4.17 (2H, q, NCH2), 3.32 (2H, dd, CHCH2), 2.81 (2H, dd, CHCH7), 1.32(3H, t, OCH2CH3), 1.25 (3H, t, NCH2CH3); andRf: 0.45 (95:5, CH2C12:CH3OH).
78%		A stirred solution of the 6-aminonaphthyridinone above (0.1 mmol), sodium sulfate (1.0 mmol), <strong>[615-13-4]2-indanone</strong> (0.15 mmol) and AcOH (7.5 ml) in dichloroethane (30 ml) under a nitrogen atmosphere was allowed to mature for 15 mins at room temperature. Sodium triacetoxyborohydride (0.15 mmol) was then added in one portion and the solution was allowed to stir for 4 h at rt (the reaction was monitored by TLC). A second addition of sodium sulfate (1.0 mmol), <strong>[615-13-4]2-indanone</strong> (0.15 mmol) and sodium triacetoxyborohydride (0.15 mmol) and stirring overnight was required to drive the reaction to completion. The reaction mixture was quenched with 10% sodium hydrogen carbonate solution and dichloromethane added to dilute the solution. The organic layer was separated from the aqueous layer and the organic layer dried (MgS04). The organic layer was concentrated in vacuo and the resulting residue patiented to silica column chromatography, gradient eluting with 100 % dichloromethane and then 1 % MeOH/dichloromethane to give an oily residue. The residue was triturated using diethyl ether and the solid was filtered off at the pump to afford a pale yellow solid (78 %). (0206) ESIMS: M+l: 378. (0207) 1H NMR (300 MHz, CDCI3) 5 8.64 (1H, s, H-2), 8.30 (1H, d,H-5), 7.55 (1H, d, H-7), 7.23-7.10 (4H, m, 4xArH), 6.69 (1H, d, NH), 4.41 (2H, q,OCH2), 4.38-4.23 (1H, m, NCH), 4.17 (2H, q, NCH2), 3.32 (2H, dd, CHCHri. 2.81 (2H, dd, CHCH2), 1.32 (3H, t, QCH9CH3)· 1.25 (3H, t, NCH2CH3).

Reference： [1]Patent: WO2008/46135,2008,A1 .Location in patent: Page/Page column 46-47
[2]Patent: WO2019/109150,2019,A1 .Location in patent: Page/Page column 37-38

50
[ 24549-12-0 ]
[ 615-13-4 ]
[ 1189545-92-3 ]

Yield	Reaction Conditions	Operation in experiment
28%	In ethylene glycol; for 10.5h;Reflux;	1-Methyl-1 ,3,4,9-tetrahydro-indeno[2,1-b]pyridin-2-one; 3-Methylamino-propionic acid methyl ester (1.5 g, 13.64 mmol) is added to a solution of 2-indanone (1.7 g, 12.86 mmol) in toluene (20 ml_) and the reaction is brought to reflux for 2.5 hours. Toluene is removed in vacuo and the residue is dissolved in ethylene glycol (17 ml_) and the resulting solution is heated to reflux for 8 hours. The reaction is allowed to cool to ambient temperature, is poured over water and extracted with dichloromethane. The organic phase is dried over magnesium sulfate and concentrated in vacuo to afford the crude title compound as a brown oil. The crude product is purified by silica gel chromatography (gradient of ethyl acetate in hexanes 10-100percent) affording 720 mg (28percent yield) of the title compound. 1H NMR (CDCI3) 52.70-2.80 (m, 4H), 3.23 (s, 3H), 3.5 (s, 2H), 7.07-7.15 (m, 2H), 7.24-7.33 (m, 1 H), 7.38 (d, 1 H, J = 7.07). MS (m/z); 199.2 (M+1).

Reference： [1]Patent: WO2009/118292,2009,A1 .Location in patent: Page/Page column 75

51
[ 1003-31-2 ]
[ 615-13-4 ]
C₁₄H₁₁NOS [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 10824 - 10825

52
[ 2491-20-5 ]
[ 615-13-4 ]
methyl (S)-2-(2,3-dihydro-1H-indan-2-ylamino)propanoate hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With 4-methyl-morpholine; palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; under 3000.3 Torr; for 12h;Inert atmosphere;	General procedure: Under Ar, 10% Pd-C (500 mg) was added to a solution of alpha-amino acid ester hydrochloride 1a-e,g,h (10 mmol) in a mixture of methanol (30 mL), symmetrical ketone (10 mmol)§ or propionaldehyde (0.87 mL, 12 mmol), and 4-methylmorpholine (4 drops). The hydrogenation vessel was flushed five times with hydrogen, and the mixture was hydrogenated (4 bar of H2, rt) for 12 h. The catalyst was removed by filtration through a fritted funnel and washed with methanol (10 mL). The combined filtrate was evaporated in vacuo to give crude 2a,b,d-h,j-p in quantitative yields. The oily compound 2f was used for further transformations without purification. The solid compounds 2a,b,d,e,g,h,j-p were suspended in ethyl acetate (50 mL), the suspensions were stirred at rt for 1 h, and the precipitate was collected by filtration to give purified compounds 2a,b,d,e,g,h,j-p.The following compounds were prepared in this manner.

Reference： [1]Tetrahedron Asymmetry,2011,vol. 22,p. 629 - 640

53
[ 253-52-1 ]
[ 615-13-4 ]
[ 243-17-4 ]

Yield	Reaction Conditions	Operation in experiment
26%	Stage #1: PHTHALAZINE; 2-indanone With pyrrolidine; 9,10-dimethyl-9,10-dibora-9,10-dihydroanthracene In diethylene glycol dimethyl ether at 110℃; for 60h; Inert atmosphere; Stage #2: With 3-chloro-benzenecarboperoxoic acid In diethylene glycol dimethyl ether at -78 - 20℃; Inert atmosphere;

Reference： [1]Kessler, Simon N.; Neuburger, Markus; Wegner, Hermann A. [European Journal of Organic Chemistry, 2011, # 17, p. 3238 - 3245]

54
[ 100-63-0 ]
[ 615-13-4 ]
[ 3254-91-9 ]

Yield	Reaction Conditions	Operation in experiment
79%		5,10-dihydroindeno[1,2-b]indole (Compound 9): A modified version of the method reported by Okamoto, et al. was employed. Okamoto, T. A.; Kobayashi, S. M.; Yamamoto, H. N., DE1952019, 1970. To a solution of <strong>[615-13-4]2-indanone</strong> (16.3 g, 123 mmol) in ethanol (80 mL) was added phenyl hydrazine (12.1 mL, 123 mmol) followed by acetic acid (12 drops) at room temperature. While stirring, the solution was warmed to reflux (oil bath at 85 C.) for 15 minutes at which point it was removed from the oil bath and allowed to cool to room temperature. Light yellow needle-like crystals precipitated from the solution. Upon cooling to room temperature, the solution was cooled to 0 C. for 30 minutes. The crystals were filtered via vacuum filtration and used without further purification. The crystals were added to a 500 mL Erlenmeyer flask and dissolved in 250 mL conc. HCl. This solution was heated to reflux (oil bath at 95 C.) and vigorously stirred for 10 minutes. As the reaction proceeded the product began to precipitate out of solution. The solution was cooled to room temperature and poured into 300 mL of water and the product precipitated as a brown solid. The solid was collected by vacuum filtration, azeotroped once with toluene and concentrated in vacuo to a brown powder (20. g, 97 mmol, 79%). The product was purified by recrystallization from acetone. Either the recrystallized product or the unpurified material was used in the next step, but we observed a minimal loss in yield for the next step using the unpurified material. 1HNMR (500 MHz, CDCl3) delta 8.35 (1 H, br s), 7.65 (1 H, d, J=7.0 Hz), 7.55 (1 H, d, J=7.0 Hz), 7.48-7.43 (m, 2 H), 7.34 (1 H, t, J=7.5 Hz), 7.24-7.16 (3 H, m), 3.74 (2 H, s): 13CNMR (125 MHz, CDCl3) delta 148.0, 143.5, 140.5, 135.1, 126.7, 125.7, 125.0, 121.9, 120.4, 119.1, 117.5, 112.2, 30.5.
	With acetic acid; In hydrogenchloride; ethanol; water;	5,10-dihydroindeno[1,2-b]indole (Compound 9): A modified version of the method reported by Okamoto, et al. was employed. Okamoto, T. A.; Kobayashi, S. M.; Yamamoto, H. N., DE1952019, 1970. To a solution of <strong>[615-13-4]2-indanone</strong> (16.3 g, 123 mmol) in ethanol (80 mL) was added phenyl hydrazine (12.1 mL, 123 mmol) followed by acetic acid (12 drops) at room temperature. While stirring, the solution was warmed to reflux (oil bath at 85 C.) for 15 minutes at which point it was removed from the oil bath and allowed to cool to room temperature. Light yellow needle-like crystals precipitated from the solution. Upon cooling to room temperature, the solution was cooled to 0 C. for 30 minutes. The crystals were filtered via vacuum filtration and used without further purification. The crystals were added to a 500 mL Erlenmeyer flask and dissolved in 250 mL conc. HCl. This solution was heated to reflux (oil bath at 95 C.) and vigorously stirred for 10 minutes. As the reaction proceeded the product began to precipitate out of solution. The solution was cooled to room temperature and poured into 300 mL of water and the product precipitated as a brown solid. The solid was collected by vacuum filtration, azeotroped once with toluene and concentrated in vacuo to a brown powder (20. g, 97 mmol, 79%). The product was purified by recrystallization from acetone. Either the recrystallized product or the unpurified material was used in the next step, but we observed a minimal loss in yield for the next step using the unpurified material. 1HNMR (500 MHz, CDCl3) delta 8.35 (1H, br s), 7.65 (1H, d, J=7.0 Hz), 7.55 (1H, d, J=7.0 Hz), 7.48-7.43 (m, 2H), 7.34 (1H, t, J=7.5 Hz), 7.24-7.16 (3H, m), 3.74 (2H, s): 13CNMR (125 MHz, CDCl3) delta 148.0, 143.5, 140.5, 135.1, 126.7, 125.7, 125.0, 121.9, 120.4, 119.1, 117.5, 112.2, 30.5.

Reference： [1]Patent: US8519122,2013,B2 .Location in patent: Page/Page column 34
[2]Patent: US2011/207147,2011,A1

55
[ 62-53-3 ]
[ 615-13-4 ]
[ 33237-72-8 ]

Yield	Reaction Conditions	Operation in experiment
89.8%	With sodium tris(acetoxy)borohydride; acetic acid; In dichloromethane; at 20℃; for 16h;Cooling with ice;	Example 6 General procedure for preparation of N-(indan-2-yl)phenylamine (compound 7) To a stirred solution of <strong>[615-13-4]2-indanone</strong> (5 g, 37.83 mmol) in DCM (135 mL) were successively added aniline (3.4 mL, 37.83 mmol), AcOH (2.16 mL, 37.83 mmol) and Na(OAc)3BH (11.22 g, 52.96 mmol) portion-wise at ice cold conditions. The reaction mixture was stirred at rt for 16 hours. The reaction mixture was then diluted with EtOAc (450 mL) and washed with water (150 mL) and brine (50 mL). The organic layer was dried over Na2SO4, filtered and concentrated. The crude material was purified by Combiflash chromatography and eluted with 1.7% EtOAc in hexane to obtain compound 7. Yield: 7.1 g (89.80%); 1H-NMR (400 MHz, DMSO-d6): delta 7.24-7.21 (m, 2H), 7.15-7.13 (m, 2H), 7.08 (t, J=8 Hz, 2H), 6.61 (d, J=8 Hz, 2H), 6.53 (t, J=7 Hz, 1H), 5.83 (d, J=7 Hz, 1H), 4.24-4.16 (m, 1H), 3.28 (dd, J=16, 7 Hz, 2H), 2.79 (dd, J=16, 7 Hz, 2H);LCMS: [M+H]=210.2, RT=3.72 minutes (Program P1, Column Y).
89.8%	With sodium tris(acetoxy)borohydride; acetic acid; In dichloromethane; at 20℃; for 16h;Cooling with ice;	Example 6: General procedure for preparation of N-(indan-2-yl)phenylamine (compound 7) To a stirred solution of <strong>[615-13-4]2-indanone</strong> (5 g, 37.83 mmol) in DCM (135 mL) were successively added aniline (3.4 mL, 37.83 mmol), AcOH (2.16 mL, 37.83 mmol) and Na(OAc)3BH (11.22 g, 52.96 mmol) portion-wise at ice cold conditions. The reaction mixture was stirred at rt for 16 hours. The reaction mixture was then diluted with EtOAc (450 mL) and washed with water (150 mL) and brine (50 mL). The organic layer was dried over Na2S04, filtered and concentrated. The crude material was purified by Combiflash chromatography and eluted with 1.7% EtOAc in hexane to obtain compound 7. Yield: 7.1 g (89.80%); 1H-NMR (400 MHz, DMSO-<): delta 7.24-7.21 (m, 2H), 7.15-7.13 (m, 2H), 7.08 (t, J= 8 Hz, 2H), 6.61 (d, J= 8 Hz, 2H), 6.53 (t, J= 7 Hz, 1H), 5.83 (d, J= 7 Hz, 1H), 4.24- 4.16 (m, 1H), 3.28 (dd, J= 16, 7 Hz, 2H), 2.79 (dd, J= 16, 7 Hz, 2H); LCMS: [M+H] = 210.2, RT = 3.72 minutes (Program PI, Column Y).

Reference： [1]Patent: US2012/214809,2012,A1 .Location in patent: Page/Page column 65
[2]Patent: WO2014/28675,2014,A1 .Location in patent: Page/Page column 112

56
[ 615-13-4 ]
[ 22013-33-8 ]
[ 1153745-37-9 ]

Yield	Reaction Conditions	Operation in experiment
96.5%		A. N-2,3-Dihydro-benzo[1,4]dioxin-6-yl-N-indan-2-ylamine (compound 57) To a stirred solution of <strong>[615-13-4]2-indanone</strong> (2 g, 15.1 mmol) in DCE (50 mL) were added 2,3-dihydro-benzo[1,4]dioxin-6-ylamine (2.28 g, 15.1 mmol), Na(OAc)3BH (4.81 g, 22.6 mmol), AcOH (1.8 mL) successively at 0 C. and the mixture was stirred overnight at rt. The reaction mixture was dissolved in ethyl acetate and was washed with 1N NaOH, water and brine. The solution was dried over Na2SO4, filtered and concentrated. The crude material was purified by Combiflash chromatography eluting with 9-10% ethyl acetate-hexane to get compound 57. Yield: 3.9 g (96.5%); 1H-NMR (400 MHz, DMSO-d6): delta 7.21-7.11 (m, 4H), 6.60-6.56 (m, 1H), 6.14-6.11 (m, 2H), 5.41 (d, J=7 Hz, 1H), 4.16-4.02 (m, 6H), 3.32-3.21 (m, 2H), 2.77-2.71 (m, 2H);LCMS [M+H]=268.2, RT=3.54 minutes, (Program P1, Column Y).
96.5%	With sodium tris(acetoxy)borohydride; acetic acid; In 1,2-dichloro-ethane; at 0 - 20℃;	A. N-2,3-Dihydro-benzo[l,4]dioxin-6-yl-N-indan-2-ylamine (compound 57) To a stirred solution of <strong>[615-13-4]2-indanone</strong> (2 g, 15.1 mmol) in DCE (50 mL) were added 2,3-dihydro-benzo[l,4]dioxin-6-ylamine (2.28 g, 15.1 mmol), Na(OAc)3BH (4.81 g, 22.6 mmol), AcOH (1.8 mL) successively at 0C and the mixture was stirred overnight at rt. The reaction mixture was dissolved in ethyl acetate and was washed with IN NaOH, water and brine. The solution was dried over Na2S04, filtered and concentrated. The crude material was purified by Combiflash chromatography eluting with 9-10% ethyl acetate-hexane to get compound 57. Yield: 3.9 g (96.5%); 1H-NMR (400 MHz, DMSO-<): delta 7.21-7.11 (m, 4 H), 6.60-6.56 (m, 1 H), 6.14- 6.11 (m, 2 H), 5.41 (d, J = 7 Hz, 1 H), 4.16-4.02 (m, 6 H), 3.32-3.21 (m, 2 H), 2.77-2.71 (m, 2 H); LCMS [M+H] = 268.2, RT = 3.54 minutes, (Program PI, Column Y).

Reference： [1]Patent: US2012/214809,2012,A1 .Location in patent: Page/Page column 78-79
[2]Patent: WO2014/28675,2014,A1 .Location in patent: Page/Page column 138-139

57
[ 1394241-20-3 ]
[ 615-13-4 ]
[ 1394241-21-4 ]

Yield	Reaction Conditions	Operation in experiment
71%		Glacial AcOH (0.25 ml) was added to a solution of the product of Step 2 (1.46g, 4.4 mmol), lH-inden-2(3H)-one (0.46g, 4.5 mmol) and NaBH(OAc)3 (1.4g, 6.55 mmol) in anhydrous 1 ,2-dichloroethane (17 ml). The resulting mixture was stirred overnight at room temperature under N2 and to it more of NaBH(OAc)3 (0.4g, 1.9 mmol) was added. After 2 h of stirring at room temperature, the mixture was quenched by addition of IN NaOH aq (5 ml). This was diluted to 60 ml with Et20 and washed with H20 and brine. The organic phase was dried over anhydrous MgSO-j, filtered and filtrate evaporated to dryness under reduced pressure. The residue was purified by flash column chromatography (Si02, CH2C12) to give pure product as a creamy solid (1.4g, 71%). NMR (300 MHz, CDCI3) delta 7.83 (d, J = 9.0 Hz, 1H), 7.34-7.5(m, 5H), 7.12-7.2 l(m, 4H), 7.05(dd, J = 2.6, 9.0 Hz, 1H), 6.49(d, J = 2.6 Hz, 1H), 4.17(m, 1H), 4.08(m, 1H), 3.19-3.27(m 2H), 2.73-2.83(m, 2H), 2.7(s, 3H), 1.22(s, 9H)
71%	With sodium tris(acetoxy)borohydride; acetic acid; In 1,2-dichloro-ethane; at 20℃;Inert atmosphere;	Example 2: Preparation of Ethyl 6-(2,3-dihydro-lH-inden-2-ylamino)-2-methyl-4- phenylquinoline-3-carboxylate A method of Abdel-Magid et al (J. Org. Chem., 61 FontWeight="Bold" FontSize="10" 3849, 1996) was used: Glacial AcOH (0.25 ml) was added to a solution of Example 1 (1.46g, 4.4 mmol), lH-inden-2(3H)-one (0.46g, 4.5 mmol) and NaBH(OAc)3 (1.4g, 6.55 mmol) in anhydrous 1 ,2-dichloroethane (17 ml). The resulting mixture was stirred overnight at room temperature under N2 and to it more of NaBH(OAc)3 (0.4g, 1.9 mmol) was added. After 2 hours of stirring at room temperature, the mixture was quenched by addition of IN NaOHaq (5 ml). This was diluted to 60 ml with Et20 and washed with H20 and brine. The organic phase was dried over anhydrous MgS04, filtered and filtrate evaporated to dryness under reduced pressure. The residue was purified by flash column chromatography (Si02, CH2C12) to give pure product as a creamy solid (1.4 g, 71%). NMR (300 MHz, DMSO-d6) delta 7.72 (d, J = 9.0 Hz, 1H), 7.53-7.41 (m, 3H), 7.31-7.28 (m, 2H), 7.23 (dd, J = 2.7, 9.3 Hz, 1H), 7.18-7.13 (m, 2H), 7.11-7.07 (m, 2H), 6.48 (d, J = 6 Hz, 1H), 6.32 (d, J = 2.4 Hz, 1H), 4.01-3.92 (m, 3H), 3.10 (dd, J = 6.9, 15.9 Hz, 2H), 2.74 (dd, J = 4.8, 15.9 Hz, 2H), 2.52 (s, 3H), 0.84 (t, J = 7.2 Hz, 3H). LCMS, m/z 423 (M + H)+.

Reference： [1]Patent: WO2012/116415,2012,A1 .Location in patent: Page/Page column 73; 74
[2]Patent: WO2014/36595,2014,A1 .Location in patent: Page/Page column 89-90

58
[ 28144-70-9 ]
[ 615-13-4 ]
[ 878733-86-9 ]

Yield	Reaction Conditions	Operation in experiment
97%	With Amberlyst-15; In acetonitrile; at 20℃; for 0.0333333h;Irradiation; Green chemistry;	General procedure: A mixture of 2-aminobenzamide 1a-d (1.0 mmol), ketone 2 (1.2 mmol) and Amberlyst-15 (10%, w/w) in acetonitrile (5 mL) was irradiated with ultrasound (40 KHz) continuously at room temperature for the time indicated in Table 2. After completion of the reaction (indicated by TLC) the solid separated was filtered, washed by diethyl ether (2 x 5 mL), dried and treated with EtOAc (15 mL). After stirring for 10 min the mixture was filtered to remove the insoluble catalyst. The filtrate was collected and concentrated under vacuum. The solid isolated was triturated in diethyl ether, filtered and dried to give the desired product. All the products prepared (3a-t) were characterized by NMR, IR, and MS spectra and purity was determined by HPLC method.

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 495 - 501

59
[ 32658-67-6 ]
[ 615-13-4 ]
[ 1420904-43-3 ]

Yield	Reaction Conditions	Operation in experiment
97%	With Amberlyst-15; In acetonitrile; at 20℃; for 0.0333333h;Irradiation; Green chemistry;	General procedure: A mixture of 2-aminobenzamide 1a-d (1.0 mmol), ketone 2 (1.2 mmol) and Amberlyst-15 (10%, w/w) in acetonitrile (5 mL) was irradiated with ultrasound (40 KHz) continuously at room temperature for the time indicated in Table 2. After completion of the reaction (indicated by TLC) the solid separated was filtered, washed by diethyl ether (2 x 5 mL), dried and treated with EtOAc (15 mL). After stirring for 10 min the mixture was filtered to remove the insoluble catalyst. The filtrate was collected and concentrated under vacuum. The solid isolated was triturated in diethyl ether, filtered and dried to give the desired product. All the products prepared (3a-t) were characterized by NMR, IR, and MS spectra and purity was determined by HPLC method.

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 495 - 501

60
indan-2-one propane-1,3-diol ketal [ No CAS ]
[ 50-00-0 ]
[ 74-85-1 ]
[ 124-38-9 ]
[ 201230-82-2 ]
[ 694-87-1 ]
[ 32796-95-5 ]
[ 615-13-4 ]

Reference： [1]Beilstein Journal of Organic Chemistry,2013,vol. 9,p. 1668 - 1676

61
[ 615-13-4 ]
[ 694-87-1 ]
[ 32796-95-5 ]

Reference： [1]Beilstein Journal of Organic Chemistry,2013,vol. 9,p. 1668 - 1676

62
indan-2-one cis-2-butene-1,4-diol ketal [ No CAS ]
[ 124-38-9 ]
[ 201230-82-2 ]
[ 694-87-1 ]
[ 32796-95-5 ]
[ 106-99-0 ]
[ 615-13-4 ]

Reference： [1]Beilstein Journal of Organic Chemistry,2013,vol. 9,p. 1668 - 1676

63
[ 159603-71-1 ]
[ 615-13-4 ]
7’-chloro-1,3-dihydrospiro[indene-2,4’-pyrido[2,3-d][1,3]oxazin]-2’(1‘H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Step A: 7’-Chloro- 1.3 -dihydrospiroFindene-2.4’-pyridoF2.3-dl F 1.3 loxazinl-2’( 1 ‘11)-one A solution of <strong>[159603-71-1]tert-butyl (6-chloropyridin-2-yl)carbamate</strong> (2.00 g, 8.75 mmol) inTHF (3 mL) was added over 10 mm to a solution of N,N,NcN’-tetramethylethylenediamine (3.28mL, 21.9 mmol) and n-butyllithium (8.75 mL of a 2.5 M solution in hexanes, 21.9 mmol) in THF (3 mL) at -78 C. The resulting mixture was stirred at -78 C for 1 h, then warmed to -50 C and stirred for 30 mm. The reaction mixture was cooled to -78 C and a solution of 1H-inden-2(3H)- one (1.73 g, 13.1 mmol) in THF (1 mL) was added over 10 mm. The resulting suspension wasdiluted with THF (10 mL) and warmed to ambient temperature where it was stirred for 16 h,then heated at 60 C for 3 h. The mixture was partitioned between saturated aqueous sodiumbicarbonate solution and dichloromethane (3x). The combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by flashcolumn chromatography on silica gel (hexane initially, grading to 30% EtOAc in hexane) to give the title compound. MS: m/z = 287.0 (M + 1).

Reference： [1]Patent: WO2013/169565,2013,A1 .Location in patent: Page/Page column 55; 56

64
[ 120-14-9 ]
[ 615-13-4 ]
(1E,3E)-1,3-bis(3,4-dimethoxybenzylidene)-1,3-dihydroinden-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With hydrogenchloride; In acetic acid; at 40℃; for 3h;	General procedure: A total of 7 curcumin-related compounds containing inden-2-one were synthesized as previously described with modification. 27,28) A mixture of the appropriate aldehyde (0.012 mol) and the inden-2-one (0.004 mol) was dissolved in glacial acetic acid saturated with anhydrous hydrogen chloride and heated in a water bath at 40 C for 3 h, the mixture was treated with cold water and filtered. The solid obtained was then washed and dried. The crude product was recrystallized from appropriate solvents (methanol or ethanol). Curcumin was isolated from the extract of Curcuma longa LINN according to a previous report.28)

Reference： [1]Biological and Pharmaceutical Bulletin,2014,vol. 37,p. 1977 - 1981

65
[ 615-13-4 ]
[ 134-96-3 ]
(1E,3E)-1,3-bis(4-hydroxy-3,5-dimethoxybenzylidene)-1,3-dihydroinden-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With hydrogenchloride In acetic acid at 40℃; for 3h;	Synthesis of Curcumin-Related Compounds General procedure: A total of 7 curcumin-related compounds containing inden-2-one were synthesized as previously described with modification. 27,28) A mixture of the appropriate aldehyde (0.012 mol) and the inden-2-one (0.004 mol) was dissolved in glacial acetic acid saturated with anhydrous hydrogen chloride and heated in a water bath at 40 °C for 3 h, the mixture was treated with cold water and filtered. The solid obtained was then washed and dried. The crude product was recrystallized from appropriate solvents (methanol or ethanol). Curcumin was isolated from the extract of Curcuma longa LINN according to a previous report.28)

Reference： [1]Zhou, Daiying; Ding, Ning; Zhao, Suqing; Li, Dongli; Van Doren, Jeremiah; Qian, Yu; Wei, Xingchuan; Zheng, Xi [Biological and Pharmaceutical Bulletin, 2014, vol. 37, # 12, p. 1977 - 1981]

66
[ 615-13-4 ]
[ 142643-29-6 ]
tert-butyl (1-(2,3-dihydro-1H-inden-2-yl)piperidin-3-yl)methylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With sodium tris(acetoxy)borohydride; acetic acid; In 1,2-dichloro-ethane; at 20℃; for 20h;Inert atmosphere;	To a solution of starting amine 4a (0.40 g, 1.87 mmol, 1.0 equiv.) in DCE (25 mL), sodium triacetoxyborohydride (1.19 g, 5.61 mmol, 3.0 equiv.), 1H-inden-2(3H)-one (0.49 g, 3.74mmol, 2.0 equiv.) and acetic acid (0.16 mL, 2.81 mmol, 1.5 equiv.) were added sequentially, under an argon atmosphere. The resulting suspension was stirred under an argon atmosphere for 20 h. The solvent was evaporated under reduced pressure and DCM (50 mL) was added to the residue, which was transferred to a separating funnel, extracted with a saturated aqueous solution of NaHCO3 (4× 50 mL) and a saturated brine solution (50 mL), dried over anhydrous Na2SO4, and evaporated under reduced pressure. The crude product was purified by flashcolumn chromatography using DCM/MeOH = 20/1 as eluent, to obtain 0.46 g of the compound as a white solid. Yield: 74%; white solid, mp 91-93 C; Rf = 0.46 (DCM/MeOH =9/1); 1H NMR (400 MHz, CDCl3): delta 0.98 (q, J = 9.2 Hz, 1H, CH2CHAHBCH), 1.45 (s, 9H, 3× CH3), 1.55-1.65 (m, 1H, CHAHBCH2CH), 1.71-1.80 (m, 4H, NCHAHBCH +CHAHBCHAHBCH), 1.98 (td, J = 11.2, 2.6 Hz, 1H, NCHAHBCH2CH2), 2.86-2.98 (m, 4H,CH2CH(N)CH2 + CHAHBNCH2CH + CH2NHCOO), 3.02-3.17 (m, 5H, CH2CH(N)CH2 +NCHAHBCH), 4.61 (t, J = 5.8 Hz, 1H, NH), 7.11-7.18 (m, 4H, 4 × Ar-H); 13C NMR (100MHz, CDCl3): delta 24.71, 28.25, 28.36, 36.74, 36.90, 37.03, 44.39, 52.01, 56.01, 67.09, 78.84,124.16 (2 × C), 126.15 (2 × C), 141.36, 141.39, 155.94; ESI-HRMS m/z calcd. forC20H31N2O2 [M+(H)]+ 331.2386, found 331.2379; IR (KBr) upsilon = 3430, 2926, 2859, 1715,1542, 1389, 1365, 1304, 1284, 1252, 1218, 1170, 1130, 1082, 1008, 971, 893, 867, 744 cm-1.

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 4442 - 4452
[2]Journal of Medicinal Chemistry,2018,vol. 61,p. 119 - 139

67
[ 615-13-4 ]
[ 20605-43-0 ]
phenyl 2-(2,3-dihydro-1H-inden-2-yl)hydrazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	Stage #1: 2-indanone; phenyl hydrazinecarboxylate In methanol Reflux; Stage #2: With sodium cyanoborohydride In methanol; acetic acid for 16h;

Reference： [1]Ivanovich, Ryan A.; Vincent-Rocan, Jean-François; Elkaeed, Eslam B.; Beauchemin, André M. [Organic Letters, 2015, vol. 17, # 19, p. 4898 - 4901]

68
[ 358-23-6 ]
[ 615-13-4 ]
[ 256637-49-7 ]

Yield	Reaction Conditions	Operation in experiment
65%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 40℃; for 1h;Inert atmosphere;	Stirred solution of 1H-inden-2(3H)-one (1; 10g,75.6 mmol) in DCM (50 mL) was added to N, N-Diisopropylethylamine(11.73 g, 90.7 mmol, 1.2 equiv.). Triflicanhydride (25.6 g, 90.7 mmol, 1.2 equiv.) was then treateddropwise at 40C for 1 h, until the consumpion of (1) asshown by TLC and the residual mass was washed withwater and extracted with DCM. The organic layer was dried(Na2SO4) and concentrated under reduced pressure. Thecrude was then purified by column chromatography oversilica gel using 7-10% EtOAc in hexane as eluent to give thetarget compound 2 (13 g, 65% yield) as yellow oil (Rf-0.57,3:7 ethylacetate/hexane, visualized by UV light (254 nm));1H NMR (500 MHz, DMSO-d6) delta 7.37 (d, 1H, ArH), 7.26(d, 1H, ArH), 7.24 (m, 2H, ArH), 5.81 (s, 1H, = CH), 3.21(s, 2H, CH2); 13C NMR (125 MHz, DMSO-d6) delta 174.1,144.1, 142.9, 127.6, 126.1, 125.8, 125.4, 118.6, 98.5; LCMS265.21 (M+H)+. Anal. Calcd. (%) for C10H7F3O3S: C,45.46; H, 2.67; S, 12.14. Found (%): C, 45.44; H, 2.65; S,12.13.

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 9903 - 9909
[2]Journal of Chemical Sciences,2017,vol. 129,p. 249 - 258

69
[ 615-13-4 ]
[ 5235-10-9 ]
(1E,3E)-1,3-bis[(1H-indazol-3-yl)methylene]-1H-inden-2(3H)-one [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2017,vol. 2017,p. 1353 - 1364

70
[ 615-13-4 ]
[ 10111-08-7 ]
(1Z,3Z)-1,3-bis[(1H-imidazol-2-yl)methylene]-1H-inden-2(3H)-one [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2017,vol. 2017,p. 1353 - 1364

71
[ 2564-83-2 ]
[ 615-13-4 ]
(2-formylphenyl)acetic acid 2,2,6,6-tetramethylpiperidin-1-yl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With 1,10-Phenanthroline; copper(II) choride dihydrate; aniline; In acetonitrile; at 20℃; under 760.051 Torr; for 24h;	General procedure: To a tube equipped with a condenser, ketone 1, TEMPO 2, CuCl2*2H2O (10mol%), 1,10-phenanthroline monohydrate (20 mol%), aniline (10 mol%), acetonitrile(2 mL) were successively added. The mixture was stirred at 40 C under air, and monitored by TLC. Upon completion, the reaction mixture was cooled down to room temperature, dried under vacuum, and purified by column chromatography on silica gel to obtain the desired products 3 (petroleum ether : ethyl acetate = 5:1).

Reference： [1]Synlett,2017,vol. 28,p. 2163 - 2168

72
[ 530-47-2 ]
[ 615-13-4 ]
[ 7156-31-2 ]

Yield	Reaction Conditions	Operation in experiment
81%	In isopropyl alcohol; for 2.5h;Reflux;	The specific operation is as follows: Weigh 20g of 2-indanone (150mmol) was added to a 250mL two-necked flask, and then added 200mL isopropanol, the mixture was slowly stirred until the solid completely dissolved.Then 22 g of <strong>[530-47-2]1,1-<strong>[530-47-2]diphenylhydrazine hydrochloride</strong></strong> (150 mmol) were slowly added. After the addition was complete, the reaction mixture was further stirred at room temperature for 30 minutes and then slowly heated to reflux with an oil bath. The mixture was refluxed for 2 hours and then quenched to room temperature , A small amount of solid precipitation.After completion of the reaction, the configuration of 50mL saturated sodium bicarbonate solution was slowly added to the resulting solution, stirring continued a large number of solid precipitation, filtration, and then were washed with sodium bicarbonate solution, water washingThe cake was dried to give 30 grams dark green solid,The above product was recrystallized from absolute ethanol to give 25 g of indeno [2,1-b] indole (yield: 81%) (placed in a glove box for later use).

Reference： [1]Patent: CN106905223,2017,A .Location in patent: Paragraph 0044; 0045

73
[ 10416-59-8 ]
[ 615-13-4 ]
[ 95683-63-9 ]

Yield	Reaction Conditions	Operation in experiment
86%	With polystyrene-bound 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine; In neat (no solvent); at 60℃; for 1h;	General procedure: Aromatic ketone (1.0mmol), BSA (244muL, 1.0mmol) and PS-BEMP (10 mol %, 45 mg or 5 mol%, 22mg) were added in a vial and stirred at 60 C for the time reported in the manuscript. The catalystwas filtered off and the mixture was washed with water. The aqueous phase was extracted withhexane (2 mL×3). The combined organic phase was washed with brine, dried with Na2SO4, filteredand then concentrated in vacuo to eliminate the acetamide by-product. The crude mixture wasthen purified to remove the reagent by flash chromatography on silica gel using hexanediethylether(99/1) as eluent to give the silyl enol ether.

Reference： [1]Synlett,2018,vol. 29,p. 126 - 130

74
[ 6092-80-4 ]
[ 615-13-4 ]
1,3-dihydro-2H-inden-2-one O-phenyl oxime [ No CAS ]

Reference： [1]Chemistry - A European Journal,2018,vol. 24,p. 594 - 598

75
[ 56990-02-4 ]
[ 615-13-4 ]
C₁₆H₁₀Br₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With sodium hydroxide; In ethanol; water; at 20℃; for 3h;	<strong>[615-13-4]2-indanone</strong> (50 g, 378 mmol) and 3,5-dibromobenzaldehyde (119.8 g, 454 mmol) were dissolved in ethanol (1500 mL) in a 3000 mL three-0 & gt; C. The aqueous solution of 8.5 M sodium hydroxide (500 mL) was slowly added thereto while maintaining the temperature at 0 C. After stirring at room temperature for 3 hours, the resulting solid was separated by vacuum filtration and washed with methanol. Dried to obtain a yellow solid compound 11-A (134.4 g, yield: 94%).

Reference： [1]Patent: KR2017/131122,2017,A .Location in patent: Paragraph 0091-0095

76
[ 628-21-7 ]
[ 615-13-4 ]
[ 1620682-15-6 ]

Yield	Reaction Conditions	Operation in experiment
69%		A solution of 66.1 g (500 mmol) of indan-2-one [615-13-4] and 340.9 g (1100 mmol) of 1,4-diiodobutane [628-21-7] in 500 ml of THF is added dropwise over the course of 2 h to a vigorously stirred mixture of 40.0 g (1 mol) of NaOH, 40 ml of water, 18.5 g (50 mmol) of tetrabutylammonium iodide [311-28-4] and 1500 ml of THF. When the addition is complete, the mixture is stirred at room temperature for a further 14 h, the aqueous phase is separated off, and the organic phase is evaporated to dryness. The residue is taken up in 1000 ml of n-heptane, washed five times with 300 ml of water each time and dried over magnesium sulfate. The crude product obtained after removal of the n-heptane is subjected to fractional distillation in an oil-pump vacuum (about 0.2 mbar, T about 135 C.). Yield: 83.0 g (345 mmol), 69%. Purity about 95% according to1H-NMR.

Reference： [1]Patent: TW2016/30884,2016,A .Location in patent: Page/Page column 81; 82

77
[ 530-47-2 ]
[ 615-13-4 ]
[ 146748-12-1 ]

Yield	Reaction Conditions	Operation in experiment
73%	In isopropyl alcohol; at 20℃; for 2.5h;Reflux;	2.65 g of 2-nonanone (20 mmol) was weighed into a 250 mL two-necked flask, then 100 mL of isopropanol was added, and the mixture was slowly stirred until the solid was completely dissolved. Then, 4.5 g of <strong>[530-47-2]1,1-<strong>[530-47-2]diphenylhydrazine hydrochloride</strong></strong> (20 mmol, 1.0 eq.) was slowly added. After the addition, the reaction mixture was further stirred at room temperature for 30 minutes, then slowly heated to reflux with an oil bath, and the mixture was refluxed for 2 hours and then stopped. Heating, cooling to room temperature, a small amount of solid precipitated.Post-treatment: 50 mL of saturated sodium bicarbonate solution was placed, slowly added to the above solution, and a large amount of solid was precipitated after stirring. The filter cake was washed with sodium bicarbonate solution and water to obtain 4.1 g of a brown solid. The yield was 73%. .

Reference： [1]Patent: CN108250252,2018,A .Location in patent: Paragraph 0096; 0097; 0098; 0099

78
[ 615-13-4 ]
[ 917391-08-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane / 0.5 h / -75 °C 1.2: 1 h / -75 - -12 °C 2.1: chlorosulfonic acid / acetonitrile / 5 h / 5 - 20 °C 3.1: hydrogenchloride / Heating / reflux 4.1: thionyl chloride / ethanol / 3.33 h / 0 - 5 °C / Heating / reflux

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2006/134112, 2006, A1

79
[ 83-33-0 ]
[ 615-13-4 ]
[ 548-35-6 ]
[ 17509-71-6 ]

Yield	Reaction Conditions	Operation in experiment
1: 61% 2: 15%	With hydrogenchloride; acetic acid at 100℃; for 12h;	Synthesis of isotruxene; general procedure 1-Indanone (10.0 g, 75.7 mmol) and 2-indanone (10.0 g, 75.7 mmol)were suspended in acetic acid (60 mL) in a 250 mL flask. Hydrochloricacid (20 mL, 6 M) was added under magnetic stirring and the mixturewas heated to 100 °C for 12 h. After cooling, the precipitate wasfiltered off, washed with water and extracted with acetone (100 mLin total). The organic phase was concentrated and the crude productwas briefly purified through a short column over silica gel and thenrecrystallised from xylene to afford isotruxene as a light yellow solid[yield 10.5 g (61%)]. The filter cake was washed with toluene andcollected to afford truxene as a yellow solid [yield 2.59 g (15%)].For 150-gram scale synthesis, 1-indanone (150 g, 1.13 mol) and2-indanone (150 g, 1.13 mol) were suspended in acetic acid (1 L) andhydrochloric acid (500 mL, 6 M) in a 3 L flask and a mechanicalstirring device was used. The mixture was heated to 100 °C for24 h and the workup procedure was similar to that described above,affording isotruxene as a light yellow solid [yield 150 g (58%)] andtruxene as a yellow solid [yield 31.1 g (12%)].Isotruxene: M.p. 219-221 °C (lit.13,14 218-220 °C); 1H NMR(400 MHz, CDCl3): δ (ppm) 8.60 (t, J = 8.0 Hz, 2 H), 7.94 (d, J = 7.2Hz, 1 H), 7.71 (d, J = 7.2 Hz, 1 H), 7.64 (t, J = 7.2 Hz, 2 H), 7.51-7.45 (m, 3 H), 7.42-7.34 (m, 3 H), 4.28 (s, 2 H), 4.01 (s, 4 H); 13C NMR(100 MHz, CDCl3): δ (ppm) 144.1, 144.0, 143.9, 142.4, 142.0, 141.8,139.1, 137.5, 136.8, 136.5, 136.1, 135.7, 126.9, 126.8, 126.5, 126.3,126.2, 126.1, 125.2, 125.1, 125.0, 123.5, 123.3, 122.1, 36.6, 35.9, 35.7;MS (EI) m/z 342 [M]+; HRMS (EI) m/z calcd for C27H18+: 342.1409;found: 342.1411.Truxene: M.p. 370-372 °C (dec.) [lit.18 368-369 °C (dec.)]; 1H NMR(500 MHz, CDCl3): δ (ppm) 7.97 (d, J = 7.5 Hz, 3 H), 7.71 (d, J = 7.5Hz, 3 H), 7.51 (t, J = 7.5 Hz, 3 H), 7.40 (t, J = 7.5 Hz, 3 H), 4.30 (s, 6 H);13C NMR (100 MHz, CDCl3): δ (ppm) 143.8, 141.7, 137.1, 135.3, 126.9,126.3, 125.1, 121.9, 36.6; MS (EI) m/z 342 [M]+; HRMS (EI) m/z calcdfor C27H18+: 342.1409; found: 342.1405.

Reference： [1]Zhou, Cen; Xuan, Wei; Luo, Shi-Peng; Bao, Yue-Hua [Journal of Chemical Research, 2018, vol. 42, # 11, p. 556 - 557]

80
[ 615-13-4 ]
[ 2975-41-9 ]

Yield	Reaction Conditions	Operation in experiment
93%	With palladium on activated charcoal; hydrogen; acetic acid; benzylamine; In isopropyl alcohol; at 80℃; under 22502.3 Torr;Autoclave;	In an autoclave, add 150g of <strong>[615-13-4]2-indanone</strong>, 145g of benzylamine, 600ml of isopropanol, and 8ml of glacial acetic acid. Add 20g of palladium-carbon catalyst, pass hydrogen to 3Mpa, and react at 80 C. After the reaction, press filter, concentrate the filtrate, and rectify 140 g of product were obtained, yield: 93%.

Reference： [1]Patent: CN110229067,2019,A .Location in patent: Paragraph 0028-0033
[2]Chemistry - A European Journal,2018,vol. 24,p. 17225 - 17229

81
[ 120-72-9 ]
[ 615-13-4 ]
1-(2,3-dihydro-1H-inden-2-yl)-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With formic acid; 10% palladium hydroxide on charcoal; In water; at 100℃; for 24h;Inert atmosphere;	In the reaction tube (20 ml) put in moderate and solder, join the indole (0.2 mmol), palladium hydroxide/carbon (10 muM %), 2 - indenone (3.0 times equivalent), subsequently the reaction tube vacuum pumping, orifice, repeatedly replacing three times, in the argon atmosphere water (0.5 ml), formic acid (2.0 times equivalent) slowly adding the reaction tube injector, the reaction tube is arranged in the 100 degree Celsius in oil bath heating and stirring the reaction. 24 Hours after stopping the reaction, the reaction tube from out in oil bath, natural cooling to room temperature, methylene chloride (15 ml) to extract respectively 3 times, the combined organic phase, saturated salt water for washing, drying with anhydrous sodium sulfate, filtered, after concentrating the filtrate by column chromatography (eluent: petroleum ether/ethyl acetate=100/1) to obtain the final product 3 v, yield 65%.

Reference： [1]Organic Letters,2019,vol. 21,p. 2302 - 2306
[2]Patent: CN109879788,2019,A .Location in patent: Paragraph 0044

82
[ 615-13-4 ]
[ 230615-52-8 ]

Reference： [1]Patent: CN109503482,2019,A

83
[ 7085-85-0 ]
[ 615-13-4 ]
[ 100-46-9 ]
1-benzyl-2-oxo-2,9-dihydro-1H,2H,9H-indeno[2,1-b]pyridine-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid In 1,2-dimethoxyethane at 120℃; for 0.25h; Microwave irradiation;	Method B: General procedure for the one-pot synthesis of N1-substituted 5,6-ring-fused 2-pyridones. General procedure: Aldehyde (1.00 eq.), ethyl cyanoacetate (1.00 eq.) and L-proline (0.10 eq.) were placed in a 10 mL microwave tube, equipped with magnetic stir bar and septum, and the mixture was heated at 80 °C for 5 minutes in the microwave oven (maximum power input: 250 W; maximum pressure: 160 PSI; power max: OFF; stirring: ON). After cooling to room temperature, TLC, eluting with petroleum ether/ethyl acetate, 8/2 (vol/vol), showed complete conversion of the aldehyde into the Knoevenagel adduct (mixture of E/Z isomers). The tube was placed in an ice water bath and allowed to cool for 5 minutes, until the intermediate became a light yellow solid, then 1,2-dimethoxyethane (1.00 mL/mmol) was added, followed by ketone (1.00 eq.), glacial acetic acid (0.10 eq.) and primary amine (1.00 eq.). The resulting reaction mixture was heated at 120 °C for 15 minutes, in the microwave oven (maximum power input: 250 W; maximum pressure: 160 PSI; power max: OFF; stirring: ON). After cooling to room temperature, TLC, eluting with petroleum ether/ethyl acetate, 1/1 (vol/vol), showed complete consumption of the Knoevenagel adduct. The reaction mixture was purified by silica gel flash chromatography, eluting with petroleum ether/ethyl acetate, from 9/1 to 1/1 (vol/vol), affording pure, target 2-pyridones (4b-e, 5a-k). 1-Benzyl-1,2,5,6,7,8-hexahydro-2-oxo-4-phenylquinoline-3-carbonitrile (4b). (Yield: 35%) Mp 87-89 C. 1H-NMR (Acetone-d6, 300 MHz) δ: 1.56-1.62 (m, 2 H), 1.72-1.80 (m, 2 H), 2.18-2.22 (t, 2 H), 2.81-2.88 (t, 2 H), 5.52 (s, 2 H), 7.28-7.34 (m, 3 H), 7.37-7.41 (m, 4 H), 7.52-7.60 (m, 3 H). HPLC/MS: found m/z [M + H]+ 341.3, [M+Na]+ 363.3, [M+K]+ 379.3, [2M+H]+ 681.5, [2M+Na]+ 703.4. Anal. calcd for C23H20N2O: C, 81.15; H, 5.92; N, 8.23, found: C 81.26, H 5.98, N 8.33.

Reference： [1]Radi, Marco; Vallerini, Gian Paolo; Petrelli, Alessia; Vincetti, Paolo; Costantino, Gabriele [Tetrahedron Letters, 2013, vol. 54, # 50, p. 6905 - 6908]

84
[ 1798-09-0 ]
[ 615-13-4 ]
1-(2-hydroxy-1H-inden-3-yl)-2-(3-methoxyphenyl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	Stage #1: m-methoxyphenylacetic acid With thionyl chloride at 60℃; for 2h; Stage #2: 2-indanone With sodium hydride In tetrahydrofuran; paraffin oil at 70℃; for 2h;	31 Synthesis of 1-(2-hydroxy-1H-inden-3-yl)-2-(3-methoxyphenyl)ethan-1-one 2-(3-methoxyphenyl)acetic acid (502 mg, 3.0 mmol) is dissolved in thionyl chloride (0.5 mL, 6.9 mmol) and the mixture is stirred at 60° C. for 2 hours. The solvent is distilled off under reduced pressure and pale yellow liquid is obtained. The pale yellow liquid and 2-indanone (529 mg, 4.0 mmol) are dissolved in dehydrated tetrahydrofuran (5 mL), and after sodium hydride 55%, (dispersed in liquid paraffin) (800 mg, 18.3 mmol) is carefully added, the mixture is stirred at 70° C. for 2 hours. After cooled to room temperature, the reaction solution is added with 1N hydrochloric acid (20 mL) and extracted with ethyl acetate, and the organic layer is washed with water. After the organic layer is dried and the solvent is distilled off under reduced pressure, the residue is purified by silica gel column chromatography (hexane:dichloromethane=1:2) and yellow solid of 400 mg is obtained in 47% yield.

Reference： [1]Current Patent Assignee: KANTO KAGAKU HOLDINGS K.K. - US2020/131193, 2020, A1 Location in patent: Paragraph 0259-0260

85
[ 5055-39-0 ]
[ 615-13-4 ]
N'-(1,3-dihydro-2H-inden-2-ylidene)-1H-indole-2-carbohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With acetic acid for 3h; Reflux;	3.1.3. Synthesis of Final Compounds 6a-i, 9a-f, and 11a,b General procedure: A solution of indole-2-carbohydrazide 4 (210 mg, 1.2 mmol) in glacial acetic acid (15 mL) was treated with the appropriate isatin derivative 5a-i and 8a-f (1.2 mmol), or ketones 10a and 10b (1.2 mmol). The resulting reaction mixture was refluxed for four hours then cooled to r.t. The obtained precipitate was collected by filtration and dried to get a powder that was recrystallized from glacial acetic acid to furnish the titled conjugates 6a-i, 9a-f, and 11a,b.

Reference： [1]Abdel-Aziz, Hatem A.; Al-Ansary, Ghada H.; Al-Warhi, Tarfah; Aljaeed, Nada; Ayyad, Rezk R.; El Kerdawy, Ahmed M.; Eldehna, Wagdy M.; Ismael, Omnia E. [Molecules, 2020, vol. 25, # 9]

86
[ 512-56-1 ]
[ 615-13-4 ]
[ 40243-62-7 ]

Yield	Reaction Conditions	Operation in experiment
87%	With sodium hydride In 1-methyl-pyrrolidin-2-one at 120℃; for 24h;	Compounds 8a-8j and 9a-9d; General Procedure General procedure: All reactions were carried out on 0.5-mmol scale. A reaction tube wascharged with NaH (3.0 equiv), carbonyl compound (1.0 equiv) andNMP (3 mL) were added followed by addition of trialkyl phosphate(3.0 equiv). Then, this reaction mixture was heated to 120 °C for 24 h.After that, the reaction mixture was diluted with Et2O, washed withwater and extracted with Et2O. The organic layer was dried overNa2SO4 and concentrated to obtain crude product which was purifiedby column chromatography (EtOAc/hexane) to afford the desiredproduct 8 and 9.

Reference： [1]Banerjee, Amit; Hattori, Tomohiro; Yamamoto, Hisashi [Synthesis, 2021]

87
[ 68295-45-4 ]
[ 615-13-4 ]
[ 2759532-58-4 ]

Yield	Reaction Conditions	Operation in experiment
55%	In methanol for 5h; Inert atmosphere; Reflux;

Reference： [1]Rufanov, Konstantin A.; Titov, Ilya Yu.; Lemenovskii, Dmitry A.; Krut'Ko, Dmitry P.; Churakov, Andrei V. [New Journal of Chemistry, 2022, vol. 46, # 3, p. 1409 - 1415]

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[ CAS No. 615-13-4 ] {[proInfo.proName]}

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Medicinal Chemistry

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[ 615-13-4 ] Synthesis Path-Upstream 1~8

[ 615-13-4 ] Synthesis Path-Downstream 1~87

Related Functional Groups of [ 615-13-4 ]

Aryls

Ketones

Precautionary Statements-General

Prevention

Response

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Related Functional Groups of
[ 615-13-4 ]