[ CAS No. 2835-98-5 ] {[proInfo.proName]}

Name: 2835-98-5|2-Amino-5-methylphenol|98%
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Quality Control of [ 2835-98-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 2835-98-5 ]

CAS No. :	2835-98-5	MDL No. :	MFCD00007693
Formula :	C₇H₉NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HCPJEHJGFKWRFM-UHFFFAOYSA-N
M.W :	123.15	Pubchem ID :	76082
Synonyms :

Calculated chemistry of [ 2835-98-5 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	2.0
Molar Refractivity :	37.84
TPSA :	46.25 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 :	Yes
Log Kp (skin permeation) :	-6.23 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.17
Log Po/w (XLOGP3) :	1.16
Log Po/w (WLOGP) :	1.29
Log Po/w (MLOGP) :	1.15
Log Po/w (SILICOS-IT) :	1.11
Consensus Log Po/w :	1.17

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.83
Solubility :	1.83 mg/ml ; 0.0149 mol/l
Class :	Very soluble
Log S (Ali) :	-1.73
Solubility :	2.31 mg/ml ; 0.0188 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.8
Solubility :	1.93 mg/ml ; 0.0157 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.0

Safety of [ 2835-98-5 ]

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 [ 2835-98-5 ]

* 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 [ 2835-98-5 ]
Downstream synthetic route of [ 2835-98-5 ]

[ 2835-98-5 ] Synthesis Path-Upstream 1~12

1
[ 3054-95-3 ]
[ 2835-98-5 ]
[ 20984-33-2 ]

Yield	Reaction Conditions	Operation in experiment
50%	With hydrogenchloride In water at 111℃; for 24 h;	General procedure: A 1N HCl solution (82.5 mL) was added to the aniline (~1 mmol) in a round bottom flask. To this was added acrolein diethyl acetal (2.5 mmol). The resulting solution was refluxed at 111 °C for 24 hours. After cooling to room temperature, the solution was neutralized (pH 7−8) by addition of solid Na2CO3. The product was then extracted into dichloromethane (3 x 100 mL), and the combined organic layers were dried over Na2SO4 and evaporated under reduced pressure. The crude residue was then purified by column chromatography (elution mixture of hexane with ethyl acetate or 15percent ethyl acetate/cyclohexane with methanol) to give the desired quinoline product.

Reference： [1] Tetrahedron Letters, 2015, vol. 56, # 46, p. 6436 - 6439

2
[ 2835-98-5 ]
[ 107-02-8 ]
[ 20984-33-2 ]

Reference： [1] Chemical Communications, 2015, vol. 51, # 84, p. 15458 - 15461

3
[ 700-38-9 ]
[ 2835-98-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogen In methanol at 23℃; for 5 h;	To a solution of 5-methyl-2-nitrophenol (1.0 g, 6.53 mmol) in methanol (10 mL) at 23° C. was added Pd/C (10 wt percent, 400 mg), and the reaction mixture was deoxygenated under vacuum, then purged with hydrogen in a balloon. After stirring for 5 h, the reaction mixture was filtered through a pad of Celite and the Celite pad was rinsed with methanol (100 mL). The filtrate was concentrated in vacuo to yield 2-amino-5-methylphenol (801 mg, 100percent).

Reference： [1] Patent: US2006/211603, 2006, A1, . Location in patent: Page/Page column 69
[2] Advanced Synthesis and Catalysis, 2013, vol. 355, # 5, p. 907 - 911
[3] Journal of Heterocyclic Chemistry, 1982, vol. 19, # 6, p. 1545 - 1547
[4] Synthesis, 2001, # 1, p. 81 - 84
[5] Justus Liebigs Annalen der Chemie, 1902, vol. 322, p. 18
[6] Journal of the American Chemical Society, 1930, vol. 52, p. 3978,3982
[7] Journal of the American Chemical Society, 1933, vol. 55, p. 3879,3882
[8] Chemische Berichte, 1921, vol. 54, p. 2496
[9] Chemische Berichte, 1921, vol. 54, p. 1315
[10] Gazzetta Chimica Italiana, 1969, vol. 99, p. 397 - 410
[11] Journal of Organic Chemistry, 1989, vol. 54, # 15, p. 3740 - 3744

4
[ 88-44-8 ]
[ 2835-98-5 ]

Reference： [1] Patent: US5847217, 1998, A,

5
[ 35605-65-3 ]
[ 2835-98-5 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 1971, vol. 44, p. 3120 - 3123

6
[ 452-86-8 ]
[ 2835-98-5 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 1971, vol. 44, p. 3120 - 3123

7
[ 74993-52-5 ]
[ 2835-97-4 ]
[ 95-71-6 ]
[ 2835-98-5 ]
[ 452-86-8 ]
[ 488-17-5 ]

Reference： [1] Journal of the American Chemical Society, 1992, vol. 114, # 25, p. 9795 - 9806

8
[ 2101-86-2 ]
[ 2835-98-5 ]

Reference： [1] Journal of the Chemical Society, 1963, p. 5571 - 5572

9
[ 196497-20-8 ]
[ 100-46-9 ]
[ 2835-98-5 ]

Reference： [1] Heterocycles, 1994, vol. 38, # 1, p. 17 - 20

10
[ 7647-01-0 ]
[ 64-19-7 ]
[ 2835-98-5 ]

Reference： [1] Chemische Berichte, 1921, vol. 54, p. 1304

11
[ 74993-52-5 ]
[ 2835-97-4 ]
[ 95-71-6 ]
[ 2835-98-5 ]
[ 452-86-8 ]
[ 488-17-5 ]

Reference： [1] Journal of the American Chemical Society, 1992, vol. 114, # 25, p. 9795 - 9806

12
[ 2835-98-5 ]
[ 14847-51-9 ]

Yield	Reaction Conditions	Operation in experiment
20%	With hydrogen bromide; sodium nitrite In water; ethyl acetate	A. 2-Bromo-5-methylphenol A solution of sodium nitrite (2.8 g, 41 mmol) in 5 ml water was added rapidly with stirring to an ice-cooled mixture of 6-amino-m-cresol (5.0 g, 41 mmol) and 48percent hydrobromic acid (17 ml, 100 mmol). The temperature was kept below 10° C. by addition of ice chips. The diazonium salt solution was then added in portions over a period of 30 min to a boiling mixture of copper(I) bromide (6.4 g, 22 mmol) and 48percent hydrobromic acid (5 ml). The resulting mixture was refluxed for an additional 30 min, then was cooled and extracted with ether (2*100 ml). The combined organic extracts were washed with water, dried over magnesium sulfate, and evaporated. The residue was chromatographed on silica gel using 98:2 hexanes/ethyl acetate to afford 233A (1.6 g, 20percent) as an oil.

Reference： [1] Patent: US2002/143024, 2002, A1,
[2] Patent: US6638937, 2003, B2,
[3] Journal of the American Chemical Society, 1933, vol. 55, p. 3879,3882

[ 2835-98-5 ] Synthesis Path-Downstream 1~78

1
[ 700-38-9 ]
[ 2835-98-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogen;palladium 10% on activated carbon; In methanol; at 23℃; for 5h;	To a solution of 5-methyl-2-nitrophenol (1.0 g, 6.53 mmol) in methanol (10 mL) at 23 C. was added Pd/C (10 wt %, 400 mg), and the reaction mixture was deoxygenated under vacuum, then purged with hydrogen in a balloon. After stirring for 5 h, the reaction mixture was filtered through a pad of Celite and the Celite pad was rinsed with methanol (100 mL). The filtrate was concentrated in vacuo to yield 2-amino-5-methylphenol (801 mg, 100%).

Reference： [1]Patent: US2006/211603,2006,A1 .Location in patent: Page/Page column 69
[2]Advanced Synthesis and Catalysis,2013,vol. 355,p. 907 - 911
[3]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 1545 - 1547
[4]Synthesis,2001,p. 81 - 84
[5]Justus Liebigs Annalen der Chemie,1902,vol. 322,p. 18
[6]Journal of the American Chemical Society,1930,vol. 52,p. 3978,3982
[7]Journal of the American Chemical Society,1933,vol. 55,p. 3879,3882
[8]Chemische Berichte,1921,vol. 54,p. 2496
[9]Gazzetta Chimica Italiana,1969,vol. 99,p. 397 - 410
[10]Journal of Organic Chemistry,1989,vol. 54,p. 3740 - 3744

2
[ 97-08-5 ]
[ 2835-98-5 ]
4-chloro-3-nitro-benzenesulfonic acid-(2-hydroxy-4-methyl-anilide) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1944,vol. 66,p. 835
[2]Journal of the American Chemical Society,1944,vol. 66,p. 835

3
[ 2835-98-5 ]
[ 14847-51-9 ]

Yield	Reaction Conditions	Operation in experiment
20%	With hydrogen bromide; sodium nitrite;copper(I) bromide; In water; ethyl acetate;	A. 2-Bromo-5-methylphenol A solution of sodium nitrite (2.8 g, 41 mmol) in 5 ml water was added rapidly with stirring to an ice-cooled mixture of 6-amino-m-cresol (5.0 g, 41 mmol) and 48% hydrobromic acid (17 ml, 100 mmol). The temperature was kept below 10 C. by addition of ice chips. The diazonium salt solution was then added in portions over a period of 30 min to a boiling mixture of copper(I) bromide (6.4 g, 22 mmol) and 48% hydrobromic acid (5 ml). The resulting mixture was refluxed for an additional 30 min, then was cooled and extracted with ether (2*100 ml). The combined organic extracts were washed with water, dried over magnesium sulfate, and evaporated. The residue was chromatographed on silica gel using 98:2 hexanes/ethyl acetate to afford 233A (1.6 g, 20%) as an oil.

Reference： [1]Patent: US2002/143024,2002,A1
[2]Journal of the American Chemical Society,1933,vol. 55,p. 3879,3882

4
[ 2835-98-5 ]
[ 99-94-5 ]
[ 16155-95-6 ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: p-Toluic acid With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 0 - 20℃; for 1h; Stage #2: 2-Hydroxy-4-methylanilin In N,N-dimethyl-formamide at 20℃; for 2h; Stage #3: With toluene-4-sulfonic acid In 1-methyl-pyrrolidin-2-one at 150℃; for 4h;	3.1-3.2 Example 3 Synthesis of 2-(4-methylphenyl)-6-methylbenzoxazole, the specific steps are as follows: (1) Dissolve 13.6g of p-toluic acid in 35g of N,N-dimethylformamide, and add 22.7g of DCC and 14.9g of HOBT in batches at about 0°C.After the addition, react at room temperature for 1 hour to obtain a reaction solution. Dissolve 12.3 g of 6-amino-m-cresol in 20 g of N,N-dimethylformamide,Add slowly to the reaction solution at room temperature, and react for 2 hours at a temperature of about 5°C after the addition.HPLC detects the reaction process, the reaction is completed to obtain the condensation reaction liquid, the condensation reaction liquid is slowly added to ice water, filtered, washed, and dried to obtain the condensation intermediate, the yield is 85%; (2) Add 24g of the intermediate to 50g of N-methylpyrrolidone, add 22.4g of p-toluenesulfonic acid, raise the temperature to 150°C for reaction, and react for 4h,HPLC detects the progress of the reaction. After the reaction is complete, the reaction solution is slowly added to ice water.The solid product is separated out, filtered, rinsed with ice methanol, and dried to obtain the productThe 2-(4-methylphenyl)-6-methylbenzoxazole was 17.7 g, the yield was 80%, the purity detected by HPLC was 99.2%, and the raw material utilization rate was 67.3%.
	With boric acid

Reference： [1]Current Patent Assignee: QINGDAO BOCHUAN TEJU TECH - CN111620833, 2020, A Location in patent: Paragraph 0090-0093; 0114-0115
[2]Siegrist,A.E. [Helvetica Chimica Acta, 1967, vol. 50, p. 906 - 957]

5
[ 2835-98-5 ]
[ 74-11-3 ]
[ 16155-97-8 ]

Yield	Reaction Conditions	Operation in experiment
87%	With diphosphorus tetraiodide In acetonitrile at 80℃; Sealed tube; Inert atmosphere;	General procedure for synthesis of 2-aryl-benzimi-dazoles/2-aryl-benzoxazoles/2-aryl-benzothiazoles: General procedure: To amixture of ortho-substituted (-NH 2 or -SH or -OH) anilines(1 mmol) and aryl acids (1 mmol) in acetonitrile (2 mL) in asealed tube (10 mL) was added diphosphorus tetraiodide (0.2mmol) under nitrogen atmosphere. Then, the tube was cappedand the mixture heated in an oil bath at 80 °C with stirringuntil the reaction was complete as monitored by TLC. Afterbeing cooled to room temperature, the reaction was quenchedwith aqueous NaHCO 3 solution and extracted with ethyl acetatethree times. The combined organic layer was washed withwater and brine and then dried over anhydrous Na 2 SO 4 . Thesolvent was removed under reduced pressure and the residuewas purified by chromatography on silica gel, eluting withpetroleum ether/ethyl acetate, to afford the correspondingproduct. The products obtained were known compounds andwere identified by melting point and 1 H NMR spectroscopy.The spectral data were compared with the literature values.2-Phenyl-1H-benzimidazole (Table-2, entry 1): m.p.:290-293 °C (Lit. [21] 292-294 °C); IR (KBr, ν max , cm -1 ): 3450,3045, 1620, 1580, 1458; 1 H NMR (400 MHz, DMSO-d 6 ): δ7.08-7.14 (m, 2H), 7.31-7.5 (m, 5H), 7.96 (d, 2H), 12.80 (s,1H); 13 C NMR (DMSO-d 6 , TMS): δ 116.5, 123.1, 127.4, 128.6,129.5, 130.7, 139.0, 152.7; MS (ESI) m/z: [M+H] + 195.1.
	With boric acid

Reference： [1]Bhagat, Saket B.; Sutar, Yogesh B.; Manohar, Yogesh; Telvekar, Vikas N. [Asian Journal of Chemistry, 2018, vol. 30, # 2, p. 376 - 380]
[2]Siegrist,A.E. [Helvetica Chimica Acta, 1967, vol. 50, p. 906 - 957]

6
[ 81-54-9 ]
[ 2835-98-5 ]
[ 94988-63-3 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1984,vol. 20,p. 2234 - 2239
Zhurnal Organicheskoi Khimii,1984,vol. 20,p. 2452 - 2458

7
[ 636-94-2 ]
[ 2835-98-5 ]
2,5-bis(6-methyl-2-benzoxazolyl)phenol [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,1993,vol. 30,p. 1613 - 1622

8
[ 140-89-6 ]
[ 2835-98-5 ]
[ 23417-29-0 ]

Yield	Reaction Conditions	Operation in experiment
89%	Stage #1: potassium ethyl xanthogenate; 2-Hydroxy-4-methylanilin In glycerol at 155℃; for 0.116667h; Microwave irradiation; Stage #2: With acetic acid In ethanol; water; glycerol
65%	In ethanol for 2h; Reflux;	5.1.3.19. N-(2,6-diisopropylphenyl)-6-((6-methylbenzo[d]oxazol-2-yl)-thio)hexanamide (18) To a solution of 2-amino-6-methylphenol (636mg, 4.57mmol) in EtOH (10mL) was added potassium O-ethyl-dithiocarbonate (801mg, 5mmol). The reaction mixture was stirred at reflux temperature for 2h and allowed to cool to rt. The solvent was evaporated under reduced pressure. The residue was adjusted to acidity by adding 1-N HCl solution, and extracted with AcOEt. The organic layer was washed with brine and dried over MgSO4. The solvent was evaporated under reduced pressure. The resulting solid was crystallized from acetone/n-hexane to give 6-methylbenzo[d]oxazole-2-thiol (10) (538mg, 65%) as a yellowish brown crystal. To a solution of the thus obtained thiol (453mg, 2.5mmol) and 2e (885mg, 2.5mmol) in DMF (8 mL) were added K2CO3 (387mg, 2.8mmol) and 18-crown-6 (66mg, 0.25mmol). The reaction mixture was stirred at 80° C for 3h and diluted with water and AcOEt. The organic layer was washed sequentially with water and brine, and dried over MgSO4. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography, and eluted with acetone/n-hexane (1:5 to 3:10) to give a solid, which was recrystallized from acetone/ether/n-hexane to afford 18 (908mg, 82%) as colorless needle-like crystals.
64%	Stage #1: potassium ethyl xanthogenate; 2-Hydroxy-4-methylanilin In ethanol Reflux; Stage #2: With acetic acid In water

	In ethanol Heating;
	Stage #1: potassium ethyl xanthogenate; 2-Hydroxy-4-methylanilin In ethanol for 16h; Heating / reflux; Stage #2: With acetic acid In water	76.a a.) 6-Methylbenzoxazole-2-thiol(Haviv F. et al.: J. Med. Chem. 1988, 31, 9, 1719-28); 3.7 g (30 mmol) 2-liydroxy-4-methylaniline is suspended in 50 ml ethanol, 4.8 g (30 mmol) O-ethyl-xanthic acid potassium salt is added to it and the mixture is heated under reflux conditions for 16 hours. The solvent is removed, the residue is dissolved in water, acidified with acetic acid to pH 5, the precipitated crystals are filtered off, washed with water. 4.3 g title compound is obtained. Mp: 2090C.
	Stage #1: potassium ethyl xanthogenate; 2-Hydroxy-4-methylanilin In ethanol for 16h; Heating / reflux; Stage #2: With acetic acid In water	3.a Example 3.; iy-{3-[(3,4- Dichlorobenzyl)(methyl)ammo]propyl}-2-[(6-methyl-l,3-benzoxazol-2- yl)oxy]acetamide; In general formula (I) Ar1 stands for 3,4-dichorophenyl group, X and Z for methylene group, R1 for methyl group, Y for 1,3-propylene group, R2 for hydrogen atom, B means oxygen atom, Ar2 represent 6-methyl-l,3-benzoxazol-2-yl group.; a.) 6-Methylbenzoxazole-2-thiol(Haviv F. et al.: J. Med. Chem. 1988, 31, 9, 1719-28); 3.7 g (30 mmol) 2-hydroxy-4-methylaniline is suspended in 50 ml ethanol, 4.8 g (30 mmol) O- ethyl-xanthic acid potassium salt is added to it and the mixture is heated under reflux conditions for 16 hours. The solvent is removed, the residue is dissolved in water, acidified with acetic acid to pH 5, the precipitated crystals are filtered off, washed with water. 4.3 g title compound is obtained. Mp: 2090C.

Reference： [1]Location in patent: experimental part Deligeorgiev, Todor G.; Kaloyanova, Stefka S.; Lesev, Nedyalko Y.; Vaquero, Juan J. [Monatshefte fur Chemie, 2011, vol. 142, # 9, p. 895 - 899]
[2]Shibuya, Kimiyuki; Kawamine, Katsumi; Miura, Toru; Ozaki, Chiyoka; Edano, Toshiyuki; Mizuno, Ken; Yoshinaka, Yasunobu; Tsunenari, Yoshihiko [Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 14, p. 4001 - 4013]
[3]Location in patent: experimental part Chen, Weixuan; Huang, Ying-ju; Gundala, Sushma Reddy; Yang, Hsiuchin; Li, Minyong; Tai, Phang C.; Wang, Binghe [Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 4, p. 1617 - 1625]
[4]Haviv; Ratajczyk; DeNet; Kerdesky; Walters; Schmidt; Holms; Young; Carter [Journal of Medicinal Chemistry, 1988, vol. 31, # 9, p. 1719 - 1728]
[5]Current Patent Assignee: SANOFI - WO2007/34251, 2007, A1 Location in patent: Page/Page column 30
[6]Current Patent Assignee: SANOFI - WO2007/34253, 2007, A1 Location in patent: Page/Page column 19

9
[ 2835-98-5 ]
[ 530-62-1 ]
[ 22876-16-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	In acetonitrile; at 23 - 70℃;	To a solution of 2-amino-5-methylphenol (777 mg, 6.32 mmol) in acetonitrile (27 mL) at 23 C. was added 1,1'-carbonyldiimidazole (3.07 g, 18.9 mmol) and the reaction mixture was heated to 70 C., and stirred overnight. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate (150 mL) and H2O (100 mL). The organic layer was separated and washed with brine (100 mL), dried (MgSO4) and concentrated to yield the crude product which was purified by silica gel column chromatography (20-50% EtOAc in hexanes) to yield 6-methyl-3H-benzooxazol-2-one (853 mg, 90%).
	In dichloromethane; at 20℃; for 24h;Inert atmosphere;	General procedure: To a solution of the corresponding 2-amino phenol (1 equiv.) in dry dichloromethane was added 1,1’,-dicarbonyldiimidazole (1.1 equiv) and stirred at ambient temperature under a nitrogen atmosphere for 24 h. The reaction mixture was quenched with water and extracted with ethyl acetate (3x). The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The benzoxazolone residue was purified by silica gel chromatography.

Reference： [1]Patent: US2006/211603,2006,A1 .Location in patent: Page/Page column 69
[2]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 1545 - 1547
[3]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 4689 - 4693
[4]Journal of Medicinal Chemistry,2015,vol. 58,p. 9258 - 9272

10
[ 816-27-3 ]
[ 2835-98-5 ]
3-Amino-7-methyl-benzo[1,4]oxazin-2-one [ No CAS ]

Reference： [1]Synthesis,1997,p. 301 - 304

11
[ 3274-12-2 ]
[ 2835-98-5 ]
5-methyl-2-(p-tolylamino)phenol [ No CAS ]
5-methyl-2-(4-methyl-4-trichloromethylcyclohexa-2,5-dienylideneamino)phenol [ No CAS ]

Reference： [1]Russian Chemical Bulletin,1997,vol. 46,p. 350 - 354

12
[ 122-88-3 ]
[ 2835-98-5 ]
2-(4-Chloro-phenoxymethyl)-6-methyl-benzooxazole [ No CAS ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1997,vol. 47,p. 1393 - 1397

13
[ 75-15-0 ]
[ 2835-98-5 ]
[ 23417-29-0 ]

Yield	Reaction Conditions	Operation in experiment
94%	With potassium hydroxide In ethanol at 100℃; for 8h;	A.1.f f) 6-Methyl-benzooxazole-2-thiol (1f); 8 g (65 mmol) of 2-amino-5-methyl-phenol is placed in the presence of potash (4.37 g, 78 mmol) in a mixture of 100 mL of CS2 and 150 mL of EtOH and heated at 100°C for 8h. After reduction to dryness the medium is taken up in the water and extracted using AcOEt and after drying the organic phases are reduced to dryness. The residue is taken up by Et20 and the crystals obtained are filtered and then rinsed in petroleum ether. 10 g of beige crystals is isolated (yield: 94%). TLC silica gel 60 F 254 Merck, CH2CI2-MeOH:95-5, Rf=0.75.
94%	With potash In ethanol at 100℃; for 8h;	f f) f) 6-Methyl-benzooxazole-2-thiol (1f) 8 g (65 mmol) of 2-amino-5-methyl-phenol is placed in the presence of potash (4.37 g, 78 mmol) in a mixture of 100 mL of CS2 and 150 mL of EtOH and heated at 100° C. for 8 h. After reduction to dryness the medium is taken up in the water and extracted using AcOEt and after drying the organic phases are reduced to dryness. The residue is taken up by Et2O and the crystals obtained are filtered and then rinsed in petroleum ether. 10 g of beige crystals is isolated (yield: 94%). TLC silica gel 60 F 254 Merck, CH2Cl2-MeOH:95-5, Rf=0.75.
	With potassium hydroxide In ethanol

With potassium hydroxide In ethanol for 8h; Heating;

Reference： [1]Current Patent Assignee: PIERRE FABRE PARCIPATIONS - WO2012/69503, 2012, A1 Location in patent: Page/Page column 18
[2]Current Patent Assignee: PIERRE FABRE PARCIPATIONS - US2013/172326, 2013, A1 Location in patent: Paragraph 0077; 0078
[3]Yamada, Megumi; Sato, Yasuo; Kobayashi, Kazuko; Konno, Fukio; Soneda, Tomoko; Watanabe, Takashi [Chemical and Pharmaceutical Bulletin, 1998, vol. 46, # 3, p. 445 - 451]
[4]Sato, Yasuo; Yamada, Megumi; Yoshida, Satoshi; Soneda, Tomoko; Ishikawa, Midori; Nizato, Tetsutaro; Suzuki, Kokichi; Konno, Fukio [Journal of Medicinal Chemistry, 1998, vol. 41, # 16, p. 3015 - 3021]

14
[ 7304-32-7 ]
[ 2835-98-5 ]
[ 135810-39-8 ]

Yield	Reaction Conditions	Operation in experiment
	With AMEBA resin; 1-hydroxy-7-aza-benzotriazole; sodium tris(acetoxy)borohydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; dacarbazine; trifluoroacetic acid; trimethyl orthoformate 1.) DMF, AcOH, 8 h, 2.) 12 h, 3.) DMF, room temperature, 8 h, 4.) DMF, room temperature, 24 h, 5.) CH₂Cl₂, 30 min; Yield given; Multistep reaction;

Reference： [1]Ouyang, Xiaohu; Tamayo, Nuria; Kiselyov, Alexander S. [Tetrahedron, 1999, vol. 55, # 10, p. 2827 - 2834]

15
[ 2835-98-5 ]
[ 57-13-6 ]
[ 22876-16-0 ]

Reference： [1]Heterocycles,1999,vol. 51,p. 1929 - 1943
[2]Arzneimittel-Forschung/Drug Research,2012,vol. 62,p. 330 - 334

16
[ 2835-98-5 ]
[ 21900-42-5 ]
<i>N</i>-(2-hydroxy-4-methyl-phenyl)-2,4-dimethyl-benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate In diethyl ether at 20℃;

Reference： [1]Aki-Sener, Esin; Bingoel, Kamuran K.; Temiz-Arpaci, Oezlem; Yalcin, Ismail; Altanlar, Nurten [Il Farmaco, 2002, vol. 57, # 6, p. 451 - 456]

17
[ 2835-98-5 ]
[ 41978-69-2 ]
[ 114603-36-0 ]

Yield	Reaction Conditions	Operation in experiment
64%	With 1-methyl-pyrrolidin-2-one; 1,8-diazabicyclo[5.4.0]undec-7-ene at 180℃; for 0.05h; microwave irradiation;

Reference： [1]Dai, Wei-Min; Wang, Xuan; Ma, Chen [Tetrahedron, 2005, vol. 61, # 28, p. 6879 - 6885]

18
[ 792-74-5 ]
[ 2835-98-5 ]
C₂₈H₂₀N₂O₂ [ No CAS ]

Reference： [1]Russian Journal of Applied Chemistry,2003,vol. 76,p. 1792 - 1794

19
[ 792-74-5 ]
[ 2835-98-5 ]
biphenyl-4,4'-dicarboxylic acid bis-[(2-hydroxy-4-methyl-phenyl)-amide] [ No CAS ]

Reference： [1]Russian Journal of Applied Chemistry,2003,vol. 76,p. 1792 - 1794

20
[ 2835-98-5 ]
[ 106-93-4 ]
[ 71472-58-7 ]

Yield	Reaction Conditions	Operation in experiment
65%	With potassium carbonate In dimethyl sulfoxide at 80℃;
	With potassium carbonate In N,N-dimethyl-formamide at 125℃; for 15h;
	With potassium carbonate In N,N-dimethyl-formamide at 130℃; for 11h;	20 Synthesis of 7-methyl-3,4-dihydro-2H-1,4-benzoxazine To a solution of 2-amino-5-methylphenol (5.0 g) in N,N-dimethylformamide (50 ml), potassium carbonate (28.3 g) and 1,2-dibromoethane (10.6 ml) were added and stirred at 130°C for 11 hours. After insoluble materials were filtered off, the filtrate was diluted with ethyl acetate and washed sequentially with water and brine. The organic layer was dried over anhydrous sodium sulfate and then filtered to remove the desiccant, followed by distilling off the solvent under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluting solvent: n-hexane:ethyl acetate = 20:1 to 9:1) to give the titled compound, i.e., 7-methyl-3,4-dihydro-2H-1,4-benzoxazine (980 mg) as a brown oil. 1H NMR (300 MHz, CHLOROFORM-D) δ 2.21 (s, 3 H), 3.36-3.43 (m, 2 H), 3.59 (brs, 1 H), 4.20-4.27 (m, 2 H), 6.48-6.63 (m, 3 H).

	With potassium carbonate In tetrahydrofuran at 100℃; for 16h;	4 A solution of 2-hydroxy-4-methyl aniline (5.0 g, 40 mmol), potassium carbonate (16.56 g, 120 mmol) and 1,2-dibromoethane (3.8 g, 20 mmol) in THF (20 mL) was heated at 100 °C in pressure-gauge-steel vessel for 16h. The completion of reaction was monitored by LCMS. The reaction mixture was poured into water (40 mL) and extracted with EtOAc (250 mL). The organic layer was dried over sodium sulfate, evaporated and the residue purified by column chromatography to obtain 1.72 g of 3,4-dihydro-7-methyl-2H- benzo[b][l,4]oxazine (free base).
	With potassium carbonate In dimethyl sulfoxide at 85℃; for 0.333333h; Microwave irradiation;

Reference： [1]Fu, Ying; Qu, Li-Hua; Zhang, Shan-Shan; Ye, Fei; Zhao, Li-Xia; Gao, Shuang; Xing, Zhi-Yong [Heterocyclic Communications, 2012, vol. 18, # 3, p. 143 - 146]
[2]Mizar, Pushpak; Myrboh, Bekington [Tetrahedron Letters, 2006, vol. 47, # 44, p. 7823 - 7826]
[3]Current Patent Assignee: TAISHO PHARMACEUTICAL HOLDINGS CO., LTD. - EP2172453, 2010, A1 Location in patent: Page/Page column 15
[4]Current Patent Assignee: PFIZER INC - WO2011/103460, 2011, A1 Location in patent: Page/Page column 234
[5]Fu, Ying; Gao, Shuang; Gao, Ying-Chao; Guo, Ke-Liang; Li, Juan-Juan; Wang, Zi-Wei; Ye, Fei; Zhao, Li-Xia [Journal of Agricultural and Food Chemistry, 2020, vol. 68, # 39, p. 10550 - 10559]

21
[ 2835-98-5 ]
[ 563-76-8 ]
[ 114603-36-0 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane at 20℃; for 3h;

Reference： [1]Lagu, Bharat; Pio, Barbara; Lebedev, Rimma; Yang, Maria; Pelton, Patricia D. [Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 12, p. 3497 - 3503]

22
[ 2835-98-5 ]
[ 71472-58-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: aq. NaHCO₃ 3: KOH
	Multi-step reaction with 2 steps 1.1: N-benzyl-N,N,N-triethylammonium chloride; sodium hydrogencarbonate / chloroform / 0 - 55 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 6 h / 0 °C / Heating / reflux 2.2: 0 - 40 °C
	Multi-step reaction with 2 steps 1: tetrahydrofuran / 2 h / 100 °C / Autoclave 2: hydrogen bromide / water / 3 h / Reflux

	Multi-step reaction with 3 steps 1.1: 2,6-di-tert-butyl-4-methyl-phenol; sodium hydrogencarbonate / tetrahydrofuran / 0.5 h / 20 °C / Industrial scale 1.2: 7 h / 5 - 12 °C / Industrial scale 2.1: potassium carbonate; 2,6-di-tert-butyl-4-methyl-phenol / tetrahydrofuran / 18 h / 60 - 65 °C / Industrial scale 3.1: borane-THF / tetrahydrofuran / 16 h / 0 - 60 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: sodium hydrogencarbonate / tetrahydrofuran; water / 4 h 2: sodium hydroxide / acetonitrile / 25 - 30 °C 3: sodium hydroxide; water / 25.5 h / Reflux; Inert atmosphere
	Multi-step reaction with 3 steps 1: sodium hydrogencarbonate / tetrahydrofuran; water / 4 h 2: potassium carbonate / 24 h / Reflux 3: sodium hydroxide; water / 25.5 h / Reflux; Inert atmosphere
	Multi-step reaction with 3 steps 1: sodium hydrogencarbonate / tetrahydrofuran; water / 4 h 2: potassium carbonate / 48 h / Reflux 3: sodium hydroxide; water / 25.5 h / Reflux; Inert atmosphere
	Multi-step reaction with 3 steps 1: sodium hydrogencarbonate / tetrahydrofuran; water / 4 h 2: caesium carbonate; tetrabutylammomium bromide / acetonitrile / 20 h / 70 °C 3: sodium hydroxide; water / 25.5 h / Reflux; Inert atmosphere
	Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 145 °C / Autoclave; Large scale 2: hydrogen bromide / 3 h / Reflux
	Multi-step reaction with 2 steps 1: tetrahydrofuran / 2 h / 100 °C / Autoclave 2: hydrogen bromide / 3 h / Reflux

Reference： [1]Kotha, Sambasivarao; Bindra, Vandana; Kuki, Atsuo [Heterocycles, 1994, vol. 38, # 1, p. 5 - 8]
[2]Current Patent Assignee: JAPAN TOBACCO INC - US2008/64871, 2008, A1
[3]Current Patent Assignee: BP P.L.C. - WO2019/129590, 2019, A1
[4]Current Patent Assignee: BP P.L.C. - WO2019/129588, 2019, A1
[5]Current Patent Assignee: BP P.L.C. - WO2019/129589, 2019, A1
[6]Current Patent Assignee: BP P.L.C. - WO2019/129589, 2019, A1
[7]Current Patent Assignee: BP P.L.C. - WO2019/129589, 2019, A1
[8]Current Patent Assignee: BP P.L.C. - WO2019/129589, 2019, A1
[9]Current Patent Assignee: BP P.L.C. - WO2020/260417, 2020, A1
[10]Current Patent Assignee: BP P.L.C. - WO2020/260417, 2020, A1

23
[ 2835-98-5 ]
[ 22876-16-0 ]

Reference： [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 1937 - 1939

24
[ 2835-98-5 ]
[ 4619-74-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: aqueous H₂SO₄ / Diazotization_.Eintragen der Diazoniumsalz-Loesung in eine heisse Loesung von CuBr in wss. HBr unter gleichzeitigem Durchleiten von Wasserdampf 2: chloroform; bromine / Behandeln unter Kuehlung 3: tetrachloromethane; bromine / Bildung unter Kuehlung

Reference： [1]Huston; Peterson [Journal of the American Chemical Society, 1933, vol. 55, p. 3879,3882]

25
[ 1603-41-4 ]
[ 19013-37-7 ]
[ 2835-98-5 ]
(3R)-5-[(2-hydroxy-4-methylphenyl)amino]-3-methyl-5-oxo-pentanoic Acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium hydroxide; boric acid In hexane; ethyl acetate; toluene	1 Preparation of Compound 2. (3R)-5-[(2-hydroxy-4-methylphenyl)amino]-3-methyl-5-oxo-pentanoic Acid Preparation of Compound 2. (3R)-5-[(2-hydroxy-4-methylphenyl)amino]-3-methyl-5-oxo-pentanoic Acid A suspension of 2-amino-5-methylphenol (4.11 g, 33.34 mmol), methyl R-(+)-3-methylglutarate (5.359, 33.34 mmol), boric acid (0.102 g, 1.65 mmol), and 2-amino-5-methylpyridine (0.178 g, 1.65 mmol) in 70 mL of dried toluene was heated at reflux (110° C.) under nitrogen for 4 hour during which water (0.66 mL) produced in the reaction was removed by azeotropic distillation in a Dean-Stark separation unit. Thin layer chromatography on silica gel (eluant: EtOAc/heptane: 1/1) revealed that the reaction was complete. The reaction mixture was cooled to about 40° C. and a 2N aqueous solution of NaOH (34 mL, 68 mmol) was added. The reaction was heated at reflux for 4 hours. The reaction mixture was cooled to room temperature, and diluted with ethyl acetate (100 mL) and water (50 mL). The mixture was stirred for 30 minutes, and the layers were separated. The aqueous layer was washed with two portions of ethyl acetate (100 mL). After careful separation, the aqueous layer was chilled to 5° C., and acidified with a 10% solution of hydrochloric acid (24 mL, 70 mmol) to afford a solid that was filtered, washed with hexane, and dried under vacuum. The solid was triturated with 100 ml of a mixture of hexane and ethyl acetate (90/10: v/v). The solid was filtered and dried in vacuo, affording the desired product (6.29 g, 75%) as an off-white solid. HPLC (Column: Higgins Kromasil 100 C18, water/acetonitrile/acetic acid: 950/50/1, 3 mL/min, 220 nm Retention time (Rt) 3.73 min. Melting point 117-118 C. H NMR(DMSO d6, 300 MHz) δ: 0.95 (d, 3H), 2.10 (m, 1H), 2.11-2.40 (m, 7H), 6.58 (d, 1H), 6.86 (s, 1H), 7.47(d, 2H). Anal. Calculated for C13H17NO4: C, 62.14; H, 6.82; N, 5.57. Found: C, 62.01; H, 6.75; N, 5.49.

Reference： [1]Current Patent Assignee: NOVO NORDISK A/S - US2003/220226, 2003, A1

26
[ 2516-96-3 ]
[ 2835-98-5 ]
[ 135810-39-8 ]

Yield	Reaction Conditions	Operation in experiment
11.3 g (42%)	With sodium hydroxide; thionyl chloride; sodium acetate In 1,4-dioxane; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; water	6.a a a 2-Nitro-7-methyl-dibenzo[b,f][1,4]oxazepin-11(10H)-One A mixture of 20.2 g (0.1 mole) of 2-chloro-5-nitrobenzoic acid and 8.4 ml thionyl chloride in 100 ml of dioxane was refluxed for 90 minutes. The solution was cooled to 50° C. and added to a suspension of 12.3 g (0.1 mole) of 2-amino-5-methyl phenol in 50 ml of water. After about half of the acid chloride was added, 8.2 g sodium acetate was added, then the rest of the acid chloride was added dropwise. The reaction mixture was stirred for 45 minutes at 50° C. Ice water was added to the mixture with stirring, and the resulting precipitate was filtered and washed with water. The filter cake was dissolved in 150 ml of water containing 4 g of NaOH and stirred for 1 hour at 85°-95° C., then cooled to room temperature. The cooled solution was acidified with HCl, filtered, and washed with water. The precipitate was dried to yield 11.3 g (42%) of 2-nitro-7-methyldibenz[b,f][1,4]oxazepin-11(10H)-one, mp 264°-266° C.

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - US5571806, 1996, A

27
[ 88-44-8 ]
[ 2835-98-5 ]

Yield	Reaction Conditions	Operation in experiment
		The composition of the isolated product was determined by HPLC and is as follows: The yield of 2-amino-5-methyl-phenol is 60% of theory, based on 2-amino-5-methyl-benzenesulphonic acid used.

Reference： [1]Patent: US5847217,1998,A

28
[ 565-74-2 ]
[ 2835-98-5 ]
[ 112808-66-9 ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: 2-bromoisovaleric acid; 2-Hydroxy-4-methylanilin With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In 1,2-dichloro-ethane Stage #2: With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 6h;	9.A Example 9; 3-[3-(4-Ethyl-2-isopropyl-7-methyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4-trifluoromethoxy-phenyl]-acrylic acid (Compound 9); A. 2-Isopropyl-7-methyl-4H-benzo[1,4]oxazin-3-one (Compound 9A); A solution of 6-amino-m-cresol (1.0 g, 8.1 mmol) in 10 mL of dry dichloroethane is add to a prestirred solution of 2-bromo-3-methylbutyic acid (1.61 g, 8.9 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.71 g, 8.9 mmol) in 20 mL of dry dichloroethane. The reaction stirred overnight before quenching with water (50 mL) and extracting with chlrorform (3×50 mL). The combined organic layers were dried with sodium sulfate, filtered and excess solvent removed on the rotary evaporator. The crude solid was then dissolved in 15 mL of dry DMF and treated with cesium carbonate (5.86 g, 18 mmol) and heated to 80° C. for 6 hours. The reaction mixture was then cooled and quenched with 50 mL of water and extracted with chloroform (3×50 mL). The combined organic layers were dried with sodium sulfate, filtered and excess solvent removed on the rotary evaporator. The crude product was then purified using flash chromatography (10% EtOAc/hexanes) to yield 1.08 g (65%) of product as an off white solid. MS (electrospray): mass calculated for C12H15NO2, 205.11; m/z found 206.1 [M+H]+.

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - US2007/78129, 2007, A1 Location in patent: Page/Page column 23-24

29
[ 2835-98-5 ]
[ 74974-54-2 ]
[ 143708-33-2 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-Hydroxy-4-methylanilin; 2-chloro-1,1,1-trimethoxyethane With acetic acid for 24h; Reflux; Stage #2: With sulfuric acid at 100℃; for 2h; Stage #3: With potassium carbonate In water	3.a To 2-amino-5-methyl-phenol (2 g) in acetic acid (20 niL) and was added 2-chloro- 1,1,1 - trimethoxy-ethane (3.01 g) and the mixture heated under reflux for 24h. The solvent was removed under reduced pressure and the residue treated with cone, sulfuric acid (5 mL). The brown solution was heated a 1000C for 2h, cooled to room temperature and quenched into water (200 mL). The mixture was made basic by the addition of solid potassium carbonate and the products extracted into diethyl ether (2 x 150 mL). The dried extracts were concentrated to an oil and the oil purified by flash column chromatography using diethyl ether / rsÃ¸hexane (3 : 7) to afford the sub-titled compound as an oil (0.170 g).1H NMR (400 MHz, DMSO) Î' 7.60 (IH, d), 7.35 (IH, q), 7.18 (IH, dt), 4.74 (2H, s), 2.50 (3H, s).
	Stage #1: 2-Hydroxy-4-methylanilin; 2-chloro-1,1,1-trimethoxyethane With acetic acid for 24h; Reflux; Stage #2: With sulfuric acid at 100℃; for 2h; Stage #3: With potassium carbonate In water	26.a Example 26: (R)-l-(6-Methyl-benzooxazol-2-ylmethyl)-3-(l-phenyl- cycloheptanecarbonyloxy)-l-azonia-bicyclo[2.2.2]octane chloridea) 2-Chloromethyl-6-methyl-benzooxazole To 2-amino-5 -methyl-phenol (2 g) in acetic acid (20 mL) and was added 2-chloro- 1,1,1 - trimethoxy-ethane (3.01 g) and the mixture heated under reflux for 24h. The solvent was removed under reduced pressure and the residue treated with cone, sulfuric acid (5 mL). The brown solution was heated a 1000C for 2h, cooled to room temperature and quenched into water (200 mL). The mixture was made basic by the addition of solid potassium carbonate and the products extracted into diethyl ether (2 x 150 mL). The dried extracts were concentrated to an oil and the oil purified by flash column chromatography using diethyl ether / z'søhexane (3 : 7) to afford the sub-titled compound as an oil (0.170 g).1H NMR (400 MHz, DMSO) δ 7.60 (IH, d), 7.35 (IH, q), 7.18 (IH, dt), 4.74 (2H, s), 2.50 (3H, s).

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC; CHARLES RIVER LABORATORIES INTERNATIONAL INC - WO2009/153536, 2009, A1 Location in patent: Page/Page column 34-35
[2]Current Patent Assignee: CHARLES RIVER LABORATORIES INTERNATIONAL INC; ASTRAZENECA PLC; FORD RHONAN - WO2009/139709, 2009, A1 Location in patent: Page/Page column 67-68

30
[ 2835-98-5 ]
[ 122-51-0 ]
[ 10531-80-3 ]

Yield	Reaction Conditions	Operation in experiment
76%	for 4h;Reflux;	General procedure: A mixture of 2-aminophenol derivative (5 mmol) and triethyl orthoformate (15 mL) was heated at reflux for 4 h. After cooling to room temperature, remained triethyl orthoformate was removed under reduced pressure and the residue was purified by column chromatography on silica gel.
64%	at 150℃; for 8h;Inert atmosphere;	General procedure: A solution of substituted 2-aminophenol (20 mmol) in triethyl orthoformate (30 mL) was heated to 150C for 8 h under argon. The mixture was cooled to room temperature and the triethyl orthoformate was removed by distillation under reduced pressure. The resulting residue was purified by silica gel column chromatography to afford substituted benzoxazole.

Reference： [1]Organic Letters,2011,vol. 13,p. 522 - 525
[2]Organic Letters,2013,vol. 15,p. 940 - 943
[3]Angewandte Chemie - International Edition,2011,vol. 50,p. 11511 - 11515
[4]Angewandte Chemie - International Edition,2009,vol. 48,p. 9127 - 9130
[5]Tetrahedron Letters,2012,vol. 53,p. 4588 - 4590
[6]Tetrahedron Letters,2015,vol. 56,p. 511 - 513
[7]Chemical Communications,2011,vol. 47,p. 11522 - 11524
[8]Chemical Communications,2012,vol. 48,p. 5181 - 5183

31
[ 32315-10-9 ]
[ 2835-98-5 ]
[ 22876-16-0 ]

Yield	Reaction Conditions	Operation in experiment
83%	With triethylamine; In tetrahydrofuran; at 0 - 20℃;	A solution of triphosgene (1.93g, 6.5mmol) in anhydrous THF (40mL) was added to a solution of 2-amino-5-methylphenol (10g, 8.1mmol) and Et3N (2.3mL) in anhydrous THF (40mL) at 0C. The resulting solution was stirred at room temperature (RT) for overnight and was diluted with water (10mL). After 30min, the reaction mixture was concentrated in vacuo and the residue was extracted with ethyl acetate (50mL×3). The combined organic layer was washed by saturated sodium chloride solution for three times, dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford 6-methylbenzo[d]oxazol-2(3H)-one as an off-white solid. Yield 83% (1.93g). MS (ESI): 150.1 [M+H]+
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0℃;Inert atmosphere;	Synthesis of 3-benzyl-6-methyl-3H-benzooxazol-2-one (2)A solution of 2-amino-5-methyl-phenol (1.0 gm, 8.1 mmol) in CH2Cl2 (30 ml) was cooled to 0 0C. Triphosgene (721 mg, 2.43 mmol) was added followed by diisopropylethylamine (7.0 ml, 17.6 mmol) and the reaction mixture was stirred under nitrogen atmosphere for 2 h. The reaction mixture was washed with water and brine. The organic phase was dried over anhydrous MgSO4 and evaporated under vacuum. The crude product 6- methylbenzo[d]oxazol-2(3H)-one was used for the next step without any purification.

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 115,p. 191 - 200
[2]Patent: WO2010/21693,2010,A2 .Location in patent: Page/Page column 33-34

32
[ 1850-14-2 ]
[ 2835-98-5 ]
[ 57260-71-6 ]
[ 1224119-94-1 ]

Yield	Reaction Conditions	Operation in experiment
94%	With acetic acid In chloroform at 60℃;	4 In accordance with the invention, substituted 2-aminobenzoxazoles can be prepared in one pot using commercially available tetramethyl orthocarbonate (2 eq, Aldrich), an amine (2 eq), and an optionally substituted 2-aminophenol (1 eq). The reaction maybe carried out in the presence of acetic acid (4 eq) in chloroform at 60°C (using a sealed tube for volatile amines). Tetramethyl orthocarbonate can be successfully replaced by its tetraethyl analogue in this reaction. Other useful solvents for the reaction include methanol, ethanol, isopropyl alcohol, acetonitrile, tetrahydrofuran, ethyl acetate, toluene, and combinations thereof.The mild reaction conditions permit the reaction to be applied to compounds with sensitive functional groups, for example, esters. The reaction is clean, providing virtually spot-to-spot conversion from an aminophenol to a 2-methoxybenzoxazole to a 2-aminobenzoxazole. The work-up and purification is straightforward and easy; in many cases, a simple re-crystallization may be sufficient for purification of final compounds. The reaction is versatile, as is demonstrated by the variety of amine reactants listed in TABLE 1. As shown by the structures included in TABLE 2, electron donating and withdrawing substituents on the 2-aminophenol are also well tolerated. The reaction by-products are methanol and, optionally, acetic acid. A simplified work-up may only involve concentration under reduced pressure, which makes the reaction particularly amenable to large-scale production. The reaction can be carried out in a variety of solvents, including methanol, acetonitrile, tetrahydrofuran, ethyl acetate, and toluene. Optionally, the solvent may include an acid such as acetic acid. However the reaction proceeds in good yield in chloroform without acetic acid.
50%	Stage #1: tetramethoxymethane; 2-Hydroxy-4-methylanilin; 1-t-Butoxycarbonylpiperazine With acetic acid In chloroform at 60℃; for 16h; Inert atmosphere; Stage #2: With sodium hydroxide In chloroform; water at 20℃; Inert atmosphere;

Reference： [1]Current Patent Assignee: CURIA INC - WO2010/48514, 2010, A1 Location in patent: Page/Page column 9
[2]Cioffi, Christopher L.; Lansing, John J.; Yueksel, Hamza [Journal of Organic Chemistry, 2010, vol. 75, # 22, p. 7942 - 7945]

33
[ 2516-96-3 ]
[ 2835-98-5 ]
[ 140413-39-4 ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: 2-chloro-5-nitrobenzoic acid With thionyl chloride In N,N-dimethyl-formamide Reflux; Stage #2: 2-Hydroxy-4-methylanilin With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 48h; Cooling;	88 Example 88 7-Methyl-2-nitro-dibenzo[b,f][1,4]oxazenin-11(10H)one (Compound No: BJ4) A slurry of 2-chloro-5-nitrobenzoic acid (1.00g, 5mmol) and SOCl2 (1.2 ml, 14mmol), containing 1 drop of DMF, was heated under reflux to obtain a yellow-brown solution. Excess SOCl2 was removed by evaporation under reduced pressure, and the residue was dissolved in THF (5ml). The resultant acid chloride solution was added dropwise over 30 min to a solution of 6-amino-m-cresol (0.611g, 5mmol) and (i-Pr)2NEt (1.73ml), 10mmol) in THF (5 ml) under ice bath. The reaction mixture was allowed to react at room tempreture for 48 h, the reaction mixture was extracted with Et2O (20ml), washed successively with 1 N HCl, saturated aqueous NaHCO3, and saturated brine, dried over MgSO4, filtered and evaporated by a rotatory evaporator to obtain a yellow oil (1.30g, 85%). mp 190-193°C. 1NMR (300MHz, d6-DMSO): δ 2.23 (s, 3H), 6.65 (d, 1H, J =8.1Hz), 6.73 (s, 1H), 7.64 (d, 1H, J =8.1Hz), 7.84 (d, 1H, J =9.0Hz), 8.31 (d, d, 1H, J =3.0, 9.0Hz), 8.43 (d, 1H, J =3.0Hz), 9.65 (br s, 1H), 9.89 (br s, 1H).

Reference： [1]Current Patent Assignee: AB ORIGINE - EP2199295, 2010, A1 Location in patent: Page/Page column 34

34
[ 1593-08-4 ]
[ 2835-98-5 ]
[ 1204887-50-2 ]

Reference： [1]Journal of Coordination Chemistry,2010,vol. 63,p. 307 - 314
[2]Polyhedron,2010,vol. 29,p. 3014 - 3020

35
[ 2835-98-5 ]
[ 7693-46-1 ]
[ 22876-16-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 5811 - 5814

36
[ 2835-98-5 ]
[ 135636-66-7 ]
[ 155601-65-3 ]
[ 1360427-70-8 ]

Yield	Reaction Conditions	Operation in experiment
68%		A mixture of <strong>[155601-65-3]2,6-difluoronicotinaldehyde</strong> (2 g, 13.9 mmol), 2-amino-5-methylphenol (1.7 g, 13.8 mmol) and 2,3-butanedione monoxime (1.065 g, 10.5 mnol) in acetic acid (120 mL) was heated at 120 C for 1.5 hours. After cooling down to room temperature, zinc powder (2 g) was added and the mixture heated one hour at 120 C and left overnight at room temperature. The suspension is then filtered and filtrate is reduced to about 20 mL. Water was added (about 100 mL) and aqueous KOH was added up to pH ~ 8. The mixture was extracted with dichloromethane and the crude obtained purified by column chromatography using CH2Cl2/Et2O as eluent. The ligand was obtained as a beige solid (2.14 g, yield 68 %) 1H NMR (CDCl3, 400 MHz): delta 8.28 (t, J= 8.0 Hz, 1H); 7.25 (d, J= 1.6 Hz, 1H); 7.09 (d, J= 8.4 Hz, 1H); 6.99 (ddd, J= 8.0, 2.0, 0.8 Hz, 1H); 6.79 (dd, J= 8.4, 2.8 Hz, 1H); 2.27 (s, 3H); 2.24 (d, J= 0.8 Hz, 3H); 2.19 (d, J= 0.8 Hz, 3H).
68%		<strong>[155601-65-3]2,6-difluoronicotinaldehyde</strong> was obtained as described in M. Schlosser and T. Rausis, Eur. J. Org. Chem. 2004, 1018.A mixture of <strong>[155601-65-3]2,6-difluoronicotinaldehyde</strong> (2 g, 13.9 mmol), 2-amino-5- methylphenol (1.7 g, 13.8 mmol) and 2,3-butanedione monoxime (1.065 g, 10.5 mmol) in acetic acid (120 mL) was heated at 120C for 1.5 hours. After cooling down to room temperature, zinc powder (2 g) was added and the mixture heated one hour at 120C and left overnight at room temperature. The suspension is then filtered and filtrate is reduced to about 20 mL. Water was added (about 100 mL) and aqueous KOH was added up to pH ~ 8. The mixture was extracted with dichloromethane and the crude obtained purified by column chromatography using CH2Cl2/Et20 as eluent. The ligand was obtained as a beige solid (2.14 g, yield 68 %).1H MR (CDC13, 400 MHz) : delta 8.28 (t, J= 8.0 Hz, IH) ; 7.25 (d, J= 1.6 Hz, IH) ; 7.09 (d, J= 8.4 Hz, IH) ; 6.99 (ddd, J= 8.0, 2.0, 0.8 Hz, IH) ; 6.79 (dd, J= 8.4, 2.8 Hz, IH) ; 2.27 (s, 3H) ; 2.24 (d, J= 0.8 Hz, 3H) ; 2.19 (d, J= 0.8 Hz, 3H).

Reference： [1]Patent: EP2423214,2012,A1 .Location in patent: Page/Page column 24
[2]Patent: WO2012/19948,2012,A1 .Location in patent: Page/Page column 32

37
[ 2835-98-5 ]
[ 186583-59-5 ]

Reference： [1]Bulletin of the Chemical Society of Japan,2012,vol. 85,p. 201 - 208

38
[ 57248-14-3 ]
[ 2835-98-5 ]
[ 1418130-85-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With pyridine In tetrahydrofuran at 15 - 20℃; for 1.5h;	2 Preparation 2. 2,5-dichloro-N-(2-hydroxy-4-methyl-phenyl)thiophene-3- carboxamide To a solution of 6-amino-m-cresol (34.14 g; 277.20 mmoles; 1.1 equiv) in THF (450 mL), add pyridine (40.76 mL; 504.00 mmoles; 2 equiv), followed by a solution of 2,5-dichlorothiophene-3-carbonyl chloride (54.30 g, 252 mmoles, 1.00 equiv) in THF (250 mL) over 30 min., using an ice-bath to maintain a temperature of 15-20°C. Stir the resulting thick mixture at room temperature for 1 hr. to give complete consumption of the aminophenol by LC-MS. Pour onto a mixture of 2 M aqueous HC1 (500 ml) and ice (250 ml) with agitation. Collect the resulting beige solid by filtration, wash well with water, and dry in air. MS (m/z): = 301.84, 303.94 (M+H)+. Dry in a vacuum oven at 40°C over P2O5 overnight to give the title intermediate (84.5g, assumed quantitative).
84.5 g	With pyridine In tetrahydrofuran at 15 - 20℃; for 1.5h;	2 Preparation 2. 2,5-dichloro-N-(2-hydroxy-4-methyl-phenyl)thiophene-3-carboxamide To a solution of 6-amino-m-cresol (34.14 g; 277.20 mmoles; 1.1 equiv) in THF(450 mL), add pyridine (40.76 mL; 504.00 mmoles; 2 equiv), followed by a solution of2,5-dichlorothiophene-3-carbonyl chloride (54.30 g, 252 mmoles, 1.00 equiv) in THF(250 mL) over 30 min., using an ice-bath to maintain a temperature of 15-20°C. Stir the5 resulting thick mixture at room temperature for 1 hr. to give complete consumption of theaminophenol by LCMS. Pour onto a mixture of 2M aqueous HCl (500 ml) and ice (250ml) with agitation. Collect the resulting beige solid by filtration, wash well with water,and dry in air. MS (m/z): = 301.84, 303.94 (M+Ht. Dry in a vacuum oven at 40°C overP20s overnight to give the title intermediate (84.5g, assume quantitative).

Reference： [1]Current Patent Assignee: ELI LILLY & CO - WO2013/9517, 2013, A1 Location in patent: Page/Page column 6
[2]Current Patent Assignee: ELI LILLY & CO - WO2014/110065, 2014, A1 Location in patent: Page/Page column 5; 6

39
[ 201230-82-2 ]
[ 2835-98-5 ]
[ 22876-16-0 ]

Reference： [1]ChemSusChem,2015,vol. 8,p. 2204 - 2211
[2]Green Chemistry,2013,vol. 15,p. 608 - 611

40
[ 10373-78-1 ]
[ 2835-98-5 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
34%	Stage #1: Camphorquinone; 2-Hydroxy-4-methylanilin In ethanol for 2h; Reflux; Stage #2: With air In ethyl acetate at 20℃; for 76h; Reflux;

Reference： [1]Nowicka-Scheibe, Joanna [Synthetic Communications, 2013, vol. 43, # 16, p. 2198 - 2207]

41
[ 2835-98-5 ]
[ 96-99-1 ]
[ 402605-84-9 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-chloro-3-nitrobenzoate With 1,3,5-trichloro-2,4,6-triazine In dichloromethane at 40℃; for 0.166667h; Microwave irradiation; Sealed tube; Stage #2: 2-Hydroxy-4-methylanilin In dichloromethane at 60℃; for 0.5h; Microwave irradiation; Sealed tube;	Typical procedure for the preparation of 4 General procedure: In a reaction tube containing a well-stirred solution of the carboxylic acid (1.83 mmol) and NEt3 (0.25 mL 1.83 mmol) in dry CH2Cl2 (3 mL), cyanuric chloride (0.11 g, 0.61 mmol) was added in small amounts at room temperature. The sealed tube was heated by microwave irradiation to 40 °C (max power 20 W) for 10 min. 2-Aminophenol (0.18 g, 1.66 mmol) was then added, and the closed vessel was irradiated at 60 °C (max power 50 W) for 30 min. Solvent was then removed by a gentle stream of nitrogen, giving a semi-solid residue. The sealed tube was then irradiated at 130 °C (max power 50 W) for 120 min. The reaction mixture was then extracted with EtOAc/DCM (1:1) and the crude products were purified by silica gel column chromatography (EtOAc/hexane 1:9 for 4a-n and 4:6 for 4o-u) to afford desired benzoxazoles.

Reference： [1]Nieddu, Giammario; Giacomelli, Giampaolo [Tetrahedron, 2013, vol. 69, # 2, p. 791 - 795]

42
[ 2835-98-5 ]
[ 104619-51-4 ]
6-methyl-1,3-benzoxazol-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	In tetrahydrofuran; for 2h;Inert atmosphere; Reflux;	Step A: 6-Methylbenzojdjoxazol-2-amine An oven-dried, round-bottomed flask was charged with <strong>[104619-51-4]di(1H-imidazol-1-yl)methanimine</strong> (1.40 g, 8.69 mmol), 2-amino-5-methylphenol (713 mg, 5.79 mmol) and anhydrous THF (20m1) at ambient temperature. The resulting suspension was refluxed under N2 (g) for 2 h to give complete conversion based on LC/MS. The solvent was removed in vacuo and the residue was purified by silica gel chromatography (0-30 % 9:1 methanol: ammonium hydroxide-chloroform) to affordthe expected product, benzo[d]oxazol-2-amine (792 mg, 5.35 mmol, 92 % yield), as agrey solid. ?H NMR (400 MHz, CHLOROFORM-cl) ppm 7.19 - 7.34 (1 H, m), 7.11(1 H, s), 7.01 (1 H, d, J=7.8 Hz), 5.60 (2 H, br. s.), 2.43 (3 H, s). MS (LC/MS) R.T.= 0.89; [M-I-H] = 149.09.
92%	In tetrahydrofuran; for 2h;Inert atmosphere; Reflux;	An oven-dried, round-bottomed flask was chargedwith di(lH-imidazoI-I-yl)methanimine (1.40 g, 8.69 mmol),2-amino-5-methylphenol (713 mg, 5.79 mmol) and anhydrous THF (20 ml) at ambient temperature. The resulting suspension was refluxed underN2 (g) for 2 h. The solvent wasremoved in vacuo and the residue was purified by silica gelchromatography (0-30% 9: I methanol:annnonium hydroxide-chloroform) to afford benzo[d]oxazol-2-amine (792 mg,5.35 mmol, 92% yield), as a grey solid.

Reference： [1]Patent: WO2013/177024,2013,A1 .Location in patent: Page/Page column 64
[2]Patent: JP5714745,2015,B2 .Location in patent: Paragraph 0663; 0664

43
[ 452-62-0 ]
[ 201230-82-2 ]
[ 2835-98-5 ]
2,7-dimethyldibenzo[b,f][1,4]oxazepin-11(10H)-one [ No CAS ]

Reference： [1]Green Chemistry,2015,vol. 17,p. 2994 - 2999

44
[ 1996-30-1 ]
[ 201230-82-2 ]
[ 2835-98-5 ]
2-chloro-7-methyldibenzo[b,f][1,4]oxazepin-11(10H)-one [ No CAS ]

Reference： [1]Green Chemistry,2015,vol. 17,p. 2994 - 2999

45
[ 201230-82-2 ]
[ 1007-15-4 ]
[ 2835-98-5 ]
2-acetyl-7-methyldibenzo[b,f][1,4]oxazepin-11(10H)-one [ No CAS ]

Reference： [1]Green Chemistry,2015,vol. 17,p. 2994 - 2999

46
[ 201230-82-2 ]
[ 38573-88-5 ]
[ 2835-98-5 ]
4-fluoro-7-methyldibenzo[b,f][1,4]oxazepin-11(10H)-one [ No CAS ]

Reference： [1]Green Chemistry,2015,vol. 17,p. 2994 - 2999

47
[ 201230-82-2 ]
[ 886509-99-5 ]
[ 2835-98-5 ]
2-(difluoromethyl)-7-methyldibenzo[b,f][1,4]oxazepin-11(10H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; catacxium A In dimethyl sulfoxide at 120℃; for 24h;

Reference： [1]Shen, Chaoren; Neumann, Helfried; Wu, Xiao-Feng [Green Chemistry, 2015, vol. 17, # 5, p. 2994 - 2999]

48
[ 3054-95-3 ]
[ 2835-98-5 ]
[ 20984-33-2 ]

Yield	Reaction Conditions	Operation in experiment
50%	With hydrogenchloride; In water; at 111℃; for 24.0h;	General procedure: A 1N HCl solution (82.5 mL) was added to the aniline (~1 mmol) in a round bottom flask. To this was added acrolein diethyl acetal (2.5 mmol). The resulting solution was refluxed at 111 C for 24 hours. After cooling to room temperature, the solution was neutralized (pH 7-8) by addition of solid Na2CO3. The product was then extracted into dichloromethane (3 x 100 mL), and the combined organic layers were dried over Na2SO4 and evaporated under reduced pressure. The crude residue was then purified by column chromatography (elution mixture of hexane with ethyl acetate or 15% ethyl acetate/cyclohexane with methanol) to give the desired quinoline product.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 6436 - 6439

49
[ 2835-98-5 ]
[ 107-02-8 ]
[ 20984-33-2 ]

Reference： [1]Chemical Communications,2015,vol. 51,p. 15458 - 15461

50
[ 17282-03-0 ]
[ 201230-82-2 ]
[ 2835-98-5 ]
3,9-dimethylbenzo[b]pyrido[3,2-f ][1,4]oxazepin-5(6H)-one [ No CAS ]

Reference： [1]Catalysis Science and Technology,2015,vol. 5,p. 4433 - 4443

51
[ 201230-82-2 ]
[ 2835-98-5 ]
[ 185017-72-5 ]
2,9-dimethylbenzo[b]pyrido[3,2-f ][1,4]oxazepin-5(6H)-one [ No CAS ]

Reference： [1]Catalysis Science and Technology,2015,vol. 5,p. 4433 - 4443

52
[ 2835-98-5 ]
[ 224185-19-7 ]
C₁₄H₁₂N₂O₃ [ No CAS ]

Reference： [1]Catalysis Science and Technology,2015,vol. 5,p. 4433 - 4443

53
[ 2835-98-5 ]
[ 68-12-2 ]
[ 10531-80-3 ]

Yield	Reaction Conditions	Operation in experiment
81%	With zinc(II) acetate dihydrate; In neat (no solvent); at 120℃; under 7600.51 Torr; for 18h;Autoclave; Inert atmosphere; Green chemistry;	General procedure: Zn(OAc)2·2H2O (5.0 mol%) was transferred to a 100 mL autoclavereactor equipped with an overhead stirrer and an automatic temperature-control system. The appropriate benzene-1,2-diamine 1 (2 mmol), DMF (10.0 mmol), and PMHS (5.0 mmol)were successively introduced. The reactor was sealed, flushedthree times with N2 (10 atm), and heated to the required temperature with vigorous stirring (600 rpm). During the course ofthe reaction, an increase of pressure was observed, due to thegeneration of Me2NH and HCHO at 120 C.15 (For this reason, the protocol needs to be performed in a sealed high-pressurereactor.) When the reaction was complete, the autoclave wascooled to r.t., and the pressure generated during the reactionwas carefully released. Basic hydrolysis was then carried out atr.t. for 30 min to remove unreacted PMHS from the mixture.13aThe mixture was then extracted with EtOAc (3 × 20 mL). Thecombined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. The crude products were further purified bycolumn chromatography [silica gel (100-200 mesh), PE-EtOAc(20:4 to 10:2)]. The spectroscopic data for the products wereconsistent with those reported in the literature.

Reference： [1]Synlett,2015,vol. 26,p. 2835 - 2842

54
[ 6624-49-3 ]
[ 2835-98-5 ]
2-(3-isoquinolinyl)-6-methylbenzoxazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With polyphthalamide(PPA); at 100 - 180℃; for 4h;Inert atmosphere;	Under the system the protection of nitrogen, the dimethyl amide (PPA) 25mmol such, is placed in the reaction system, the temperature to a 100 °C the rear, the <strong>[6624-49-3]isoquinoline-3-carboxylic acid</strong> 25mmol, 6-amino-m-cresol 25mmol, added to the above-mentioned reaction solution at the same time, continue to heating to 180 °C, reaction 4 hours, to be after the reaction cooling, dichloromethane is used for extraction, using rotary evaporimeter evaporation of the solvent, to obtain 2 - (3-isoquinolyl) - 6-benzoxazole (A-1) 15.75mmol, the yield is 63percent.

Reference： [1]Patent: ,2016, .Location in patent: Paragraph 0034

55
[ 2578-45-2 ]
[ 2835-98-5 ]
2-[(3,5-dinitropyridin-2-yl)amino]-5-methylphenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With triethylamine; In methanol; at 20℃;	General procedure: Triethylamine (0.42 ml, 3 mmol) was added to a solution of 1 (0.6 g, 1 mmol) and corresponding o-aminophenol (3 mmol) in MeOH (30 ml). The reaction mixture was stirred at room temperature for 1-2 h (TLC monitoring). Then the mixture was poured into water (150 ml) and acidified with HCl to pH 5-6. The precipitate was filtered off, washed with water and dried in air.

Reference： [1]Mendeleev Communications,2016,vol. 26,p. 383 - 385

56
[ 27151-65-1 ]
[ 2835-98-5 ]
C₁₄H₁₉NO₄ [ No CAS ]

Reference： [1]Organic Syntheses,2005,vol. 81,p. 262 - 272

57
[ 137-26-8 ]
[ 2835-98-5 ]
[ 23417-29-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	In water at 80℃; Green chemistry;
75%	Stage #1: 2-Hydroxy-4-methylanilin With potassium carbonate In N,N-dimethyl-formamide for 0.0833333h; Stage #2: Thiram In N,N-dimethyl-formamide at 120℃; for 12h;	Typical procedure for the preparation of 2-mercaptobenzoxazoles in the presence of K2CO3 (TP2) General procedure: 2-Aminophenol (1.0 mmol), K2CO3 (3.0 mmol) was dissolved in DMF (3 mL) in a dried tube, equipped with a magnetic stirring bar and a septum. The mixture was stirred for 5 minutes, and then TMTD (0.6 mmol) was added. The reaction mixture was then heated at 120 °C and checked by TLC until the starting material was finished (around 12 hours). The reaction was cooled down to room temperature, and then quenched with sat. NH4Cl solution and extracted with ethyl acetate, dried over anhydrous Na2SO4 and evaporated under vacuum. The residue was purified by flash column chromatography to afford the desired product.
	In water at 80℃; for 3h;

In water at 80℃;

2-(Butylthio)benzo[d]thiazole (3a); Typical Procedure General procedure: A mixture of 2-aminobenzenethiol (1a; 1.0 mmol) and TMTD (0.6 mmol) in H2O (2.0 mL) was heated at 120 °C for 2-3 h, then K2CO3 (2.0 mmol) and 1-bromobutane (2a; 2.0 mmol) were added to the reaction mixture. The mixture was stirred at 80 °C and the reaction was monitored by TLC (about 5 h). The reaction was then quenched with aq NH4Cl, and extracted with EtOAc. The combined extracts were dried (anhyd Na2SO4) and concentrated under vacuum. The crude material was purified by column chromatography on silica gel (PE/EtOAc 10:1) to give 3a as a yellow oil.

Reference： [1]Liu, Xing; Liu, Min; Xu, Wan; Zeng, Meng-Tian; Zhu, Hui; Chang, Cai-Zhu; Dong, Zhi-Bing [Green Chemistry, 2017, vol. 19, # 23, p. 5591 - 5598]
[2]Liu, Min; Zeng, Meng-Tian; Xu, Wan; Wu, Li; Dong, Zhi-Bing [Tetrahedron Letters, 2017, vol. 58, # 46, p. 4352 - 4356]
[3]Liu, Xing; Zhang, Shi-Bo; Zhu, Hui; Dong, Zhi-Bing [Journal of Organic Chemistry, 2018, vol. 83, # 19, p. 11703 - 11711]
[4]Chen, Jin-Quan; Dong, Zhi-Bing; Guo, Jia [Synthesis, 2020, vol. 52, # 13, p. 1927 - 1933]

58
[ 352-23-8 ]
[ 2835-98-5 ]
[ 1357076-31-3 ]

Reference： [1]RSC Advances,2018,vol. 8,p. 16019 - 16023

59
[ 79424-03-6 ]
[ 2835-98-5 ]
ethyl 2-[6-methyl-2-(trifluoromethyl)-2,3-dihydrobenzo[d]oxazol-2-yl]acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With potassium carbonate; In dichloromethane; at 20℃; for 3h;Inert atmosphere; Schlenk technique;	General procedure: In a 25ml dry Schlenk flask under argon, 1.62 mmol (0.9 equiv) of catechol (or 2 amino phenol, or 2-mercaptophenol, or salicylic alcohol), 248 mg (1. 8 mmol, 1 equiv) of potassium carbonate and 3 ml of methylene chloride were introduced. After stirring for 15 min at room temperature, 1.8 mmol (1 equiv) of fluorinated alkyne 2 was added via syringe. The mixture was stirred 3 h at room temperature. The solvent was evaporated in vacuo and the crude product was purified on silica using petroleum ether/diethyl ether as eluent (95/5) or by crystallization from diethyl ether, to give the expected products 3a-j, 7 and 9a-e with good yields.

Reference： [1]Journal of Fluorine Chemistry,2018,vol. 212,p. 45 - 50

60
[ 2835-98-5 ]
[ 4551-69-3 ]
4-[(Z)-(2-hydroxy-4-methylphenylamino)phenylmethylene]-3-methyl-1-phenyl-2-pyrazolin-5-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol at 60℃; for 4h;	4-{(Z)-[4-(methoxycarbonylmethyl)phenylamino]phenylmethylene}-3-methyl-1-phenyl-2-pyrazolin-5-one (HL1) General procedure: HPMBP(0.278 g, 1.0 mmol) dissolved in 20 mL methanol was mixed withmethyl 4-aminophenylacetate (0.165 g, 1.0 mmol) dissolved in20 mL methanol and stirred for 4 h at 60 C. The solution obtainedwas filtered and the filtrate was left for slow evaporation at roomtemperature in the air. The yellow prismatic crystal formed afterapproximately 20 days.

Reference： [1]Zong, Ziao; Wei, Xiaodan; Yan, Xingchen; Fan, Yuhua [Journal of Molecular Structure, 2018, vol. 1171, p. 333 - 339]

61
[ 2835-98-5 ]
[ 51012-64-7 ]
(3SR,3a'SR,8a'RS)-2',6',7-trimethyl-3a',8a'-dihydro-1'H,2H,4H-spiro[benzo[b][1,4]oxazine-3,8'-indeno[1,2-c]pyrrole]-1',3'(2'H)-dione [ No CAS ]

Reference： [1]Organic Letters,2018

62
[ 2835-98-5 ]
[ 51012-64-7 ]
7-methyl-3-(m-tolyl)-2H-benzo[b][1,4]oxazine [ No CAS ]

Reference： [1]Organic Letters,2018

63
[ 2835-98-5 ]
[ 128-04-1 ]
[ 23417-29-0 ]

Yield	Reaction Conditions	Operation in experiment
75%	With aluminum (III) chloride In water; N,N-dimethyl-formamide at 120℃;

Reference： [1]Liu, Xing; Zhang, Shi-Bo; Dong, Zhi-Bing [European Journal of Organic Chemistry, 2018, vol. 2018, # 39, p. 5406 - 5411]

64
[ 2835-98-5 ]
[ 611-74-5 ]
[ 14016-00-3 ]

Yield	Reaction Conditions	Operation in experiment
86%	With Imidazole hydrochloride at 160℃; for 10h; Green chemistry;	2.1 General procedure for the synthesis of benzoxazole derivatives (2a -2d) General procedure: A mixture of 1a (0.6g, 5.5 mmol, 1 equiv), imidazolium chloride (0.17g, 1.65mmol,0.3equiv) and N,N-dimethylacetamide 5ml was stirred at 140 °C for 8h. When thereaction was completed. Water (15ml) and ethyl acetate (20ml) were added with stirringto the reaction mixture. The organic layer was extracted and dried over anhydrousNa2SO4, filtered and concentrated under reduced pressure. The resulting residue waspurified by column chromatography on silica gel using PE/EA as eluent to give the target product 2a.

Reference： [1]Tian, Qingqiang; Luo, Wen; Gan, Zongjie; Li, Dan; Dai, Zeshu; Wang, Huajun; Wang, Xuetong; Yuan, Jianyong [Molecules, 2019, vol. 24, # 1]

65
[ 36818-07-2 ]
[ 2835-98-5 ]
[ 1369593-50-9 ]

Yield	Reaction Conditions	Operation in experiment
	In diphenylether for 2h; Reflux;	4.1.2. General procedure for synthesis of 4-6 and 13 General procedure: Compound 2 (2.18 g, 10 mmol) and benzene-1,2-diamine (1.30 g,12 mmol) in Ph2O (10 mL) was heated to reflux for 2 h until thereaction completed (monitored by TLC). Then the mixture wascooled, filtered, and the solid was washed with petroleum ether(15mL x 3) to give 2.28 g of grey solid 4, which was used in nextstep without further purification. Compounds 5-6 and 13 weresynthesized followed the same procedure.

Reference： [1]Liu, Qing-Qing; Lu, Ke; Zhu, Hai-Miao; Kong, Shi-Lin; Yuan, Jing-Mei; Zhang, Guo-Hai; Chen, Nan-Ying; Gu, Chen-Xi; Pan, Cheng-Xue; Mo, Dong-Liang; Su, Gui-Fa [European Journal of Medicinal Chemistry, 2019, vol. 165, p. 293 - 308]

66
[ 124-38-9 ]
[ 2835-98-5 ]
[ 10531-80-3 ]

Reference： [1]Green Chemistry,2019,vol. 21,p. 1695 - 1701

67
[ 27421-51-8 ]
[ 5963-77-9 ]
[ 119072-55-8 ]
[ 2835-98-5 ]
N-(2-(tert-butylamino)-1-(1-methyl-1H-indol-2-yl)-2-oxoethyl)-N-(2-hydroxy-4-methylphenyl)pent-2-ynamide [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2019,vol. 17,p. 6284 - 6292

68
[ 590-93-2 ]
[ 119072-55-8 ]
[ 883526-76-9 ]
[ 2835-98-5 ]
N-(2-(tert-butylamino)-1-(1,5-dimethyl-1H-indol-2-yl)-2-oxoethyl)-N-(2-hydroxy-4-methylphenyl)but-2-ynamide [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2019,vol. 17,p. 6284 - 6292

69
[ 590-93-2 ]
[ 7188-38-7 ]
[ 857283-89-7 ]
[ 2835-98-5 ]
N-(2-(tert-butylamino)-2-oxo-1-(3-(pyrrolidin-1-yl)phenyl)ethyl)-N-(2-hydroxy-4-methylphenyl)but-2-ynamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With sodium sulfate In methanol at 20℃; Sealed tube;

Reference： [1]He, Yi; Wu, Danjun; Li, Zhenghua; Robeyns, Koen; Van Meervelt, Luc; Van Der Eycken, Erik V. [Organic and Biomolecular Chemistry, 2019, vol. 17, # 25, p. 6284 - 6292]

70
[ 2835-98-5 ]
C₁₈H₂₀N₂O₂ [ No CAS ]
[ 71472-58-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: 2,6-di-tert-butyl-4-methyl-phenol; sodium hydrogencarbonate / tetrahydrofuran / 0.5 h / 20 °C / Industrial scale 1.2: 7 h / 5 - 12 °C / Industrial scale 2.1: potassium carbonate; 2,6-di-tert-butyl-4-methyl-phenol / tetrahydrofuran / 18 h / 60 - 65 °C / Industrial scale 3.1: sodium bis(2-methoxyethoxy)aluminium dihydride; 2,6-di-tert-butyl-4-methyl-phenol / toluene / 30.5 h / 18 - 22 °C / Inert atmosphere; Industrial scale

Reference： [1]Current Patent Assignee: BP P.L.C. - WO2019/129588, 2019, A1

71
[ 75-45-6 ]
[ 2835-98-5 ]
[ 10531-80-3 ]

Yield	Reaction Conditions	Operation in experiment
81%	With water; potassium carbonate; In acetonitrile; at 50℃; for 12h;	As shown in Figure 4,0.2 mmol of 2-amino-5-methylphenol,0.6mmol potassium carbonate,1 mmol of water was added to the reaction tube.After removing the air and charging with chlorodifluoromethane, 2 mL of acetonitrile was injected into the reaction tube.The reaction was stirred at 50 C for 12 h.TLC and GC were followed during the reaction to determine the specific reaction time.After completion of the reaction, the mixture was cooled to room temperature, and the mixture was thoroughly mixed with ethyl acetate.After concentration, the organic phases were combined and purified with ethyl ether: ethyl acetate=100:1 eluted to afford 6-methylbenzo[d]oxazole as a yield of 81%.

Reference： [1]Patent: CN110078642,2019,A .Location in patent: Paragraph 0048-0049

72
[ 125366-78-1 ]
[ 2835-98-5 ]
C₂₈H₂₄N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88.7%	In methanol; ethyl acetate; for 1.0h;Reflux;	4,4'-Dihydroxy-1,1'-biphenyl-3,3'-dicarbaldehyde (100 mg, 0.41 mmol) was dissolved in ethyl acetate solution.Stir under heat until clear and transparent.6-Amino m-cresol (106.8 mg, 0.87 mmol) was dissolved in a methanol solution and stirred with heating until clear and transparent.An ethyl acetate solution of <strong>[125366-78-1]4,4'-dihydroxy-1,1'-biphenyl-3,3'-dicarbaldehyde</strong> is added to a solution of 6-aminom-cresol in methanol, and the mixture is heated under reflux for 1 hour.TLC monitors the reaction completely,A large amount of solid precipitated, which was suction filtered to give a red solid, which was rinsed with methanol three times and dried in vacuo.4,4'-dihydroxy-1,1'-biphenyl-3,3'-diformaldehyde 6-aminom-cresol Schiff base (165.7 mg, 0.37 mmol),The yield was 88.7%.

Reference： [1]Patent: CN110283099,2019,A .Location in patent: Paragraph 0050-0051

73
[ 52200-48-3 ]
[ 15226-74-1 ]
[ 2835-98-5 ]
[ 140413-11-2 ]

Yield	Reaction Conditions	Operation in experiment
81%	With palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In N,N-dimethyl-formamide; at 135℃; for 12h;Sealed tube; Inert atmosphere;	General procedure: Method A: A sealed tube equipped with a magnetic stir bar was charged with the corresponding 3-bromo-2-fluoropyridine (1 mmol), amino phenol (1 mmol), Pd(OAc)2 (5 mol%), xantphos (5 mol%) and DMAP (2.5 mmol). The tube was purged with argon. Then DMF (10V) was added followed by the addition of Co2(CO)8 (0.25 mmol). The tube was closed with seal plug instantly. The reaction tube was placed in a preheated oil bath at 120 0C for 8 h. On completion, the reaction mixture was cooled to room temperature, added water and ethyl acetate (1:1). Precipitated solid was filtered through a Celite bed. The bed was washed thoroughly with ethyl acetate. Organic layer was separated. Aqueous layer extracted with EtOAc. The combined organic layers were washed with water, brine, dried over anhydrous sodium sulphate. Organic layer was concentrated under reduced pressure and purified by flash column chromatography on silica gel (230-400 mesh) with ethyl acetate and petroleum ether as eluent to afford the corresponding pyridobenzoxazepinone. Method B: A sealed tube equipped with a magnetic stir bar was charged with the corresponding <strong>[52200-48-3]3-bromo-2-chloropyridine</strong> (1 mmol), amino phenol (1 mmol), Pd(OAc)2 (5 mol%), xantphos (5 mol%) and DBU (2.5 mmol). The tube was purged with argon. Then DMF (10 V) was added followed by the addition of Co2(CO)8 (0.25 mmol). The tube was closed with seal plug instantly. The reaction tube was placed in a pre heated oil bath at 135 0C for 12 h. On completion, the reaction mixture was cooled to room temperature, added water and ethyl acetate (1:1). Precipitated solid was filtered through a Celite bed. The bed was washed thoroughly with ethyl acetate. Organic layer was separated. Aqueous layer extracted with EtOAc. The combined organic layers were washed with water, brine, dried over anhydrous sodium sulphate. Organic layer was concentrated under reduced pressure and purified by flash column chromatography on silica gel (230-400 mesh) with ethyl acetate and petroleum ether as eluent to afford the corresponding pyridobenzoxazepinone.

Reference： [1]Synthetic Communications,2020,vol. 50,p. 348 - 360

74
[ 15226-74-1 ]
[ 17282-03-0 ]
[ 2835-98-5 ]
3,9-dimethylbenzo[b]pyrido[3,2-f ][1,4]oxazepin-5(6H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In N,N-dimethyl-formamide; at 135℃; for 12h;Sealed tube; Inert atmosphere;	General procedure: Method A: A sealed tube equipped with a magnetic stir bar was charged with the corresponding 3-bromo-2-fluoropyridine (1 mmol), amino phenol (1 mmol), Pd(OAc)2 (5 mol%), xantphos (5 mol%) and DMAP (2.5 mmol). The tube was purged with argon. Then DMF (10V) was added followed by the addition of Co2(CO)8 (0.25 mmol). The tube was closed with seal plug instantly. The reaction tube was placed in a preheated oil bath at 120 0C for 8 h. On completion, the reaction mixture was cooled to room temperature, added water and ethyl acetate (1:1). Precipitated solid was filtered through a Celite bed. The bed was washed thoroughly with ethyl acetate. Organic layer was separated. Aqueous layer extracted with EtOAc. The combined organic layers were washed with water, brine, dried over anhydrous sodium sulphate. Organic layer was concentrated under reduced pressure and purified by flash column chromatography on silica gel (230-400 mesh) with ethyl acetate and petroleum ether as eluent to afford the corresponding pyridobenzoxazepinone. Method B: A sealed tube equipped with a magnetic stir bar was charged with the corresponding 3-bromo-2-chloropyridine (1 mmol), amino phenol (1 mmol), Pd(OAc)2 (5 mol%), xantphos (5 mol%) and DBU (2.5 mmol). The tube was purged with argon. Then DMF (10 V) was added followed by the addition of Co2(CO)8 (0.25 mmol). The tube was closed with seal plug instantly. The reaction tube was placed in a pre heated oil bath at 135 0C for 12 h. On completion, the reaction mixture was cooled to room temperature, added water and ethyl acetate (1:1). Precipitated solid was filtered through a Celite bed. The bed was washed thoroughly with ethyl acetate. Organic layer was separated. Aqueous layer extracted with EtOAc. The combined organic layers were washed with water, brine, dried over anhydrous sodium sulphate. Organic layer was concentrated under reduced pressure and purified by flash column chromatography on silica gel (230-400 mesh) with ethyl acetate and petroleum ether as eluent to afford the corresponding pyridobenzoxazepinone.

Reference： [1]Synthetic Communications,2020,vol. 50,p. 348 - 360

75
[ 15226-74-1 ]
[ 2835-98-5 ]
[ 185017-72-5 ]
2,9-dimethylbenzo[b]pyrido[3,2-f ][1,4]oxazepin-5(6H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In N,N-dimethyl-formamide; at 135℃; for 12h;Sealed tube; Inert atmosphere;	General procedure: Method A: A sealed tube equipped with a magnetic stir bar was charged with the corresponding 3-bromo-2-fluoropyridine (1 mmol), amino phenol (1 mmol), Pd(OAc)2 (5 mol%), xantphos (5 mol%) and DMAP (2.5 mmol). The tube was purged with argon. Then DMF (10V) was added followed by the addition of Co2(CO)8 (0.25 mmol). The tube was closed with seal plug instantly. The reaction tube was placed in a preheated oil bath at 120 0C for 8 h. On completion, the reaction mixture was cooled to room temperature, added water and ethyl acetate (1:1). Precipitated solid was filtered through a Celite bed. The bed was washed thoroughly with ethyl acetate. Organic layer was separated. Aqueous layer extracted with EtOAc. The combined organic layers were washed with water, brine, dried over anhydrous sodium sulphate. Organic layer was concentrated under reduced pressure and purified by flash column chromatography on silica gel (230-400 mesh) with ethyl acetate and petroleum ether as eluent to afford the corresponding pyridobenzoxazepinone. Method B: A sealed tube equipped with a magnetic stir bar was charged with the corresponding 3-bromo-2-chloropyridine (1 mmol), amino phenol (1 mmol), Pd(OAc)2 (5 mol%), xantphos (5 mol%) and DBU (2.5 mmol). The tube was purged with argon. Then DMF (10 V) was added followed by the addition of Co2(CO)8 (0.25 mmol). The tube was closed with seal plug instantly. The reaction tube was placed in a pre heated oil bath at 135 0C for 12 h. On completion, the reaction mixture was cooled to room temperature, added water and ethyl acetate (1:1). Precipitated solid was filtered through a Celite bed. The bed was washed thoroughly with ethyl acetate. Organic layer was separated. Aqueous layer extracted with EtOAc. The combined organic layers were washed with water, brine, dried over anhydrous sodium sulphate. Organic layer was concentrated under reduced pressure and purified by flash column chromatography on silica gel (230-400 mesh) with ethyl acetate and petroleum ether as eluent to afford the corresponding pyridobenzoxazepinone.

Reference： [1]Synthetic Communications,2020,vol. 50,p. 348 - 360

76
[ 61117-58-6 ]
[ 694-80-4 ]
[ 2835-98-5 ]
[ 60344-89-0 ]

Yield	Reaction Conditions	Operation in experiment
79%	With palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 150℃; for 16h; Sealed tube; Inert atmosphere;	1.1 General procedure for the synthesis of substituted dibenzoxazepinones: General procedure: A sealed tube equipped with a magnetic stir bar was charged with the corresponding 1-bromo -2-fluoro (or chloro) benzene/ 1-fluoro-2-iodobenzene (1 mmol), amino phenol (1 mmol), Pd(OAc)2 (5 mol%), xantphos (5 mol%) and DBU (2.5 mmol). The tube was purged with argon. Then DMF (10 V) was added followed by the addition of Co2(CO)8 (0.25 mmol). The tube was closed with seal plug instantly. The reaction tube was placed in a pre heated oil bath at 150 0C for 16 h. On completion, the reaction mixture was cooled to room temperature, added water and ethyl acetate (1:1). Precipitated solid was filtered through a Celite bed. The bed was washed thoroughly with ethyl acetate. Organic layer was separated. Aqueous layer extracted with EtOAc. The combined organic layers were washed with water, brine, dried over anhydrous sodium sulphate. Organic layer was concentrated under reduced pressure and purified by flash column chromatography on silica gel (230-400 mesh) with ethyl acetate and petroleum ether as eluent to afford the corresponding dibenzoxazepinones.

Reference： [1]Anchan, Kavitha; Baburajan, Poongavanam; Puttappa, Nagaswarupa H.; Kumar Sarkar, Sujit [Synthetic Communications, 2020, vol. 50, # 3, p. 348 - 360]

77
[ 2835-98-5 ]
[ 488-17-5 ]
C₁₄H₁₁NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With copper(II) carbonate; 3,4,5-trihydroxybenzoic acid; oxygen; sodium hydrogencarbonate In water at 40℃; for 45h;	Synthesis of 2-hydroxyphenoloxazin-3-one: General procedure: In a 150 mL reactor, put 2.18 g o-aminophenol, 1.88 g catechol, 2.2 mg gallic acid, 0.3 g iron sulfate, 0.25 g copper carbonate, 80 mg NaOH and 60 mL water. Heat to 40°C with stirring, add oxygen, keep the pressure in the reactor at 0.3 MPa, stop the reaction after 20 hours of reaction, cool to room temperature, extract with 3 × 15 mL of ethyl acetate, combine ethyl acetate layers, remove by rotary evaporation Ethyl acetate, the remaining solid was recrystallized with isopropanol, suction filtered, and dried to obtain 3.6g of black solid. The structure of the product was determined to be 2-hydroxyphenoloxazin-3-one by NMR (see attached picture), MS, etc. , The yield was 87%, and the purity of the product analyzed by liquid chromatography was 98%.

Reference： [1]Current Patent Assignee: ZHENGZHOU UNIVERSITY - CN111233781, 2020, A Location in patent: Paragraph 0025; 0028

78
[ 2835-98-5 ]
[ 488-17-5 ]
2-hydroxy-4,7-dimethyl-3H-phenoxazin-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With 3,4,5-trihydroxybenzoic acid; oxygen; manganese(II) acetate; sodium hydroxide In water at 25℃; for 0.433333h; Sonication; Autoclave; Green chemistry; regioselective reaction;

Reference： [1]Li, Wenhao; Duan, Wenxue; Tang, Qingxuan; Li, Zhan-Ting; Yang, Guanyu [Green Chemistry, 2021, vol. 23, # 3, p. 1136 - 1139]

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[ CAS No. 2835-98-5 ] {[proInfo.proName]}

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[ 2835-98-5 ] Synthesis Path-Upstream 1~12

[ 2835-98-5 ] Synthesis Path-Downstream 1~78

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