148625-35-8|Methyl 3-formyl-4-nitrobenzoate| Ambeed

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Quality Control of [ 148625-35-8 ] Purity: 97% SDS Specification

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Product Details of [ 148625-35-8 ]

CAS No. :	148625-35-8
Formula :	C₉H₇NO₅
M.W :	209.16
SMILES Code :	O=C(OC)C1=CC=C([N+]([O-])=O)C(C=O)=C1
MDL No. :	MFCD05664271
Boiling Point :	No data available
InChI Key :	JHFSCEMUDKRPID-UHFFFAOYSA-N
Pubchem ID :	10867527

Safety of [ 148625-35-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 148625-35-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	6
Fraction Csp3	0.11
Num. rotatable bonds	4
Num. H-bond acceptors	5.0
Num. H-bond donors	0.0
Molar Refractivity	51.93
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	89.19 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.12
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.47
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.19
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	0.26
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-0.25
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.76

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.09
Solubility	1.68 mg/ml ; 0.00804 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.95
Solubility	0.235 mg/ml ; 0.00112 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-1.81
Solubility	3.24 mg/ml ; 0.0155 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.53 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	3.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.92

Application In Synthesis of [ 148625-35-8 ]

* 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.

Downstream synthetic route of [ 148625-35-8 ]

[ 148625-35-8 ] Synthesis Path-Downstream 1~35

1
[ 109-97-7 ]
[ 148625-35-8 ]
5,10,15,20-tetrakis(5-methoxycarbonyl-2-nitrophenyl)porphyrin [ No CAS ]

References: [1]Journal of the Chemical Society. Chemical communications,1993,p. 162 - 163.

2
[ 108763-41-3 ]
[ 148625-35-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium periodate; water; In tetrahydrofuran; at 20 - 40℃;	Step 2: 3-Formyl-4-nitro-benzoic acid methyl ester (Compound 4); [0216] Compound 3 (11. 81G 47.2 mmol) and NAI04 (30.3 g 141.6 mmol) was dissolved in 250 mL THF/H2O 1: 1 at room temperature. The dark red solution was warmed to about 40 °C while heavy precipitation occurred and the color changed to light brown. After 1 h the precipitate was removed by filtration and washed with 200 mL ethyl acetate. The organic layer was washed three times with saturated NAHC03, once with brine and dried with NA2S04. The solution was evaporated to dryness and the resulting oil was purified on a silicagel pad eluting with DCM-hexane gradient (30percent to 60percent DCM) to yield after evaporation yellow Compound 4. [0217] H'-NMR (CDC13) : S (ppm) 10.39 (s, 1H, CHO), 8.57 (d, 1H, J=2.1 Hz, AR-H2) 8.40-8. 36 (dd, 1H, J=2.1 Hz and 8.4Hz, Ar-H6), 8.14 (d, 1H, J=8. 4Hz, AR-H5), 4.00 (s, 3H, OCH3).

References: [1]Tetrahedron Letters,1994,vol. 35,p. 219 - 222.
[2]Chemical Communications,2007,p. 504 - 506.
[3]Patent: WO2005/12288,2005,A1 .Location in patent: Page/Page column 85; 125.

3
[ 109-97-7 ]
[ 104-87-0 ]
[ 148625-35-8 ]
5-(2-nitro-5-methoxycarbonylphenyl)-10,15,20-tritolylporphyrin [ No CAS ]

References: [1]European Journal of Organic Chemistry,2005,p. 5067 - 5076.

4
[ 148625-35-8 ]
[ 147804-55-5 ]
5,15-bis(5-methoxycarbonyl-2-nitrophenyl)-10,20-ditolylporphyrin [ No CAS ]

References: [1]European Journal of Organic Chemistry,2005,p. 5067 - 5076.

5
[ 148625-35-8 ]
[ 100-46-9 ]
3-[(E)-Benzylimino-methyl]-4-nitro-benzoic acid methyl ester [ No CAS ]

References: [1]Organic Letters,2006,vol. 8,p. 3999 - 4002.

6
[ 107-21-1 ]
[ 148625-35-8 ]
[ 929897-33-6 ]

References: [1]Chemical Communications,2007,p. 504 - 506.

7
[ 558-13-4 ]
[ 148625-35-8 ]
[ 886853-92-5 ]

Yield	Reaction Conditions	Operation in experiment
95.5%	With triphenylphosphine; In dichloromethane; at 0℃; for 1h;	[00173] To a solution methyl 3-fontauiyl-4-nitrobenzoate (3.137 g, 15 mmol) and CBr4 (5.48 g, 16.5 mmol) in DCM (50 mL) was dropwise added PPh3 (7.86 g, 30 mmol) solution in DCM (50 mL) at 0 0C. After addition, the mixture was stirred for 1 h and warmed to rt. The solution was filtered through a short silica gel coumn, eluted with 20percent EtOAc/hexanes. The solvent was evaporated and the residue was chromotagraphed with 10 to 20percent EtOAc/hexanes to afford the product as a slightly yellow compound (5.23 g, 95.5percent). 1H NMR (400 MHz, CDCl3) delta 8.27 (IH, t, J= 0.8 Hz), 8.19-8.13 (2H, m), 7.76 (IH, s), 3.99 (3H5 s).13C NMR (100 MHz, CDCl3) delta 164.9, 149.4, 134.7, 133.2, 133.1, 131.7, 130.6, 125.2, 94.9, 53.2. HRMS calc'd for C10H8NO4Br2 ([M]+) 363.8820. Found: 363.8823.
74%	With triphenylphosphine; In dichloromethane; at 0℃; for 1h;Inert atmosphere;	Step 1: Synthesis of methyl 3-(2,2-dibromovinyl)-4-nitrobenzoate (1) (ref. Journal of Organic Chemistry (2007), 72(4), 1341-1346) To a solution of <strong>[148625-35-8]methyl 3-formyl-4-nitrobenzoate</strong> (23.7 mmol) and carbontetrabromide (8.66 g, 26.1 mmol) in dichloromethane (50 ml) was added dropwise a solution of triphenylphosphine (12.44 g, 47.5 mmol) in dichloromethane (50 ml) at 0° C. under a nitrogen atmosphere. The reaction was stirred for 1 h at 0° C. and then allowed to warm to room temperature. A small amount of white solid was formed. The solution was concentrated to 30 mL and then filtered. The organic solvent was concentrated under reduced pressure. The crude product was purified by flash column chromatography (SiO2, 10percent EtOAc in hexanes as eluent) to afford methyl 3-(2,2-dibromovinyl)-4-nitrobenzoate was obtained as a light tan solid (32 g, 74percent); 400 M Hz 1H NMR (CDCl3) 8.26 (br s, 1H), 8.12-8.18 (m, 2H), 7.75 (s, 1H), 3.98 (s, 3H).
	With triphenylphosphine; In dichloromethane; at 0℃;	1-(2,2-dibromovinyl)-2-nitrobenzene: 2-nitrobenzaldehyde (10.00 g, 66.2 mmol) was dissolved in DCM (350 mL). CBr4 (23.04 g, 69.5 mmol) was added and the solution cooled to 0 °C in an ice bath. PPh3 (36.4 g, 139 mmol) was added in several portions, and the solution stirred at 0 °C until the reaction was complete by TLC (30 minutes). Hexanes (350 mL) were added to precipitate P(O)Ph3 and P(O)Br2Ph3, and the solution was vacuum filtered over a pad of silica gel, rinsing with 10percent EtOAc (hexanes). The filtrate was collected and solvent removed to yield pure 1-(2,2-dibromovinyl)-2-nitrobenzene (19.80 g, 97percent).

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 1341 - 1346.
[2]Patent: WO2006/47888,2006,A1 .Location in patent: Page/Page column 73; 93-94.
[3]Patent: US2010/249127,2010,A1 .Location in patent: Page/Page column 54-55.
[4]Journal of Organic Chemistry,2008,vol. 73,p. 538 - 549.
[5]Tetrahedron Letters,2011,vol. 52,p. 1815 - 1818.

8
[ 201932-92-5 ]
[ 148625-35-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium periodate; In tetrahydrofuran; water; at 20℃; for 3h;	A solution of 3-methyl-4-nitro-benzoic acid methyl ester (24.99 g, 128.1 mmol) and N,N-dimethylformamide dimethyl acetal (40.0 mL, 300 mmol) was heated at 1400C for 22.5 h. After cooling to rt, the reaction mixture was concentrated and the residue was crystallized from MeOH to give a purple solid.This solid was dissolved in THF (500 mL) and water (500 mL), and sodium periodate (62.62 g, 292.8 mmol) was added followed by additional sodium periodate (15.6 g, 72.9 mmol) two hours later. After stirring at rt for an additional 1 h, the reaction mixture was filtered through Celite washing with EtOAc (2 L). The filtrate was washed with saturated NaHCO3 (600 mL) and the organic layer was dried over Na2SO4. After filtration, the filtrate was concentrated and the residue was passed through a pad of silica gel, washing with CH2Cl2/hexanes (75percent- 100percent). The filtrate was concentrated and dried to give 3-formyl-4-nitro-benzoic acid methyl ester as yellowish solid. MS (EI): cal'd 210.0 (MH+), exp 210.2 (MH+).

References: [1]Patent: WO2007/87129,2007,A2 .Location in patent: Page/Page column 67.

9
[ 623-51-8 ]
[ 148625-35-8 ]
[ 850074-42-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 50℃;	A mixture of 4-formyl-3-nitro- benzoic acid methyl ester (15.2 g, 72.8 mmol), mercapto-acetic acid ethyl ester (8.70 mL, 79.3 mmol) and K2CO3 (12.9 g, 93.1 mmol) in 140 mL of anhydrous DMF was heated at 500C overnight. After cooling to rt, the mixture was poured into 1 L of ice-water and the resulting mixture was stirred for 40min. The solid formed was filtered and washed with 4*70 mL of water. After drying, benzo[b]thiophene-2,6- <n="69"/>dicarboxylic acid 2-ethyl ester 6-methyl ester was obtained as a pale solid. 1H NMR (CDCI3, 200 MHz) delta 8.56 (s, IH), 8.09-7.97 (m, 2H), 7.88 (d, J= 8.0 Hz, IH), 4.40 (q, J= 7.2 Hz, 2H), 3.95 (s, 3H), 1.40 (t, J = 6.8 Hz, 3H). MS (EI): cal'd 265.0 (MH+), exp 265.0 (MH+).

References: [1]Patent: WO2007/87129,2007,A2 .Location in patent: Page/Page column 67-68.

10
[ 2365-48-2 ]
[ 148625-35-8 ]
[ 7345-76-8 ]

Yield	Reaction Conditions	Operation in experiment
323 mg	With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 3h;	12223] A mixture of 1.00 g of methyl 3-formyl-4-nitroben- zoate, 609 mg of methyl thioglycolate, 761 mg of potassium carbonate, and 15 ml of N,N-dimethylformamide was stirred for 3 hours at 60° C. The reaction mixture was cooled to room temperature, water was added to the reaction mixture, and extraction was performed three times with ethyl acetate. The collected organic layer was washed with water and saturated saline, dried over magnesium sulfate, and then concentrated under reduced pressure. The residues were subjected to silica gel colunm chromatography, thereby obtaining 323 mg of dimethyl benzo[b]thiophene-2,5-dicarboxylate (hereinafter, described as a ?compound 58 of the present invention?).12224] Compound 58 of the Present Invention12225] ?H-NMR (CDC13) oe: 8.60-8.56 (m, 1H), 8.13-8.10 (m, 2H), 7.93-7.91 (m, 1H), 3.97 (s, 3H), 3.97 (s, 3H)
323 mg	With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 3h;	A mixture of 1.00 g of <strong>[148625-35-8]methyl 3-formyl-4-nitrobenzoate</strong>, 609 mg of methyl thioglycolate, 761 mg of potassiumcarbonate, and 15 ml of N,N-dimethylformamide was stirred for 3 hours at 60°C. The reaction mixture was cooled toroom temperature, water was added to the reaction mixture, and extraction was performed three times with ethyl acetate.The collected organic layer was washed with water and saturated saline, dried over magnesium sulfate, and thenconcentrated under reduced pressure. The residues were subjected to silica gel column chromatography, thereby obtaining323 mg of dimethyl benzo[b]thiophene-2,5-dicarboxylate.

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4562 - 4567.
[2]Patent: US2015/282482,2015,A1 .Location in patent: Paragraph 2223; 2224; 2225.
[3]Patent: EP2926660,2015,A1 .Location in patent: Paragraph 0362.

11
[ 107-59-5 ]
[ 148625-35-8 ]
[ 850073-97-1 ]

Yield	Reaction Conditions	Operation in experiment
		Benzo thiophene-2, 5-dicarboxylic acid 2-tert-butyl ester 5-methyl ester. To a suspension of sodium sulfide (7.95 g, 102 mmol) in anhydrous DMF (200 mL) at 0°C were added acetic acid (5.80 mL, 102 mmol) and additional DMF (100 mL). The mixture was allowed to stir at 0 °C for 30 min and chloro-acetic acid tert-butyl ester (14. 6 mL, 102 mmol) was added followed by additional DMF (50 mL). The resulting mixture was allowed to stir at 0 °C for 30 min and at rt for 30 min. To this mixture were added K2CO3 (16.4 g, 119 mmol) and <strong>[148625-35-8]3-formyl-4-nitro-benzoic acid methyl ester</strong> (17.68 g, 84.55 mmol) in DMF (30 mL). The resulting mixture was heated at 55.'C for 22 h, cooled to rt and poured into water (1.2 L). The solid formed was filtered, washed with water (300 mL) and crystallized from MeOH to give benzo [b] thiophene-2, 5-dicarboxylic acid 2-tert-butyl ester 5-methyl ester as a pale solid. MS (EI) : cal'd 237.0 (M-'butyl+H+), exp 237.1 (M-'butyl+H+).

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4562 - 4567.
[2]Patent: WO2005/34880,2005,A2 .Location in patent: Page/Page column 86; 87.

12
[ 207862-97-3 ]
[ 148625-35-8 ]

References: [1]Tetrahedron,2008,vol. 64,p. 688 - 695.

13
[ 148625-35-8 ]
[ 850073-98-2 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4562 - 4567.
[2]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4562 - 4567.
[3]Patent: WO2006/115845,2006,A1 .
[4]Patent: WO2005/34880,2005,A2 .

14
[ 148625-35-8 ]
C₁₁H₈SO₄ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4562 - 4567.

15
[ 148625-35-8 ]
[ 850073-99-3 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4562 - 4567.
[2]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4562 - 4567.
[3]Patent: WO2005/34880,2005,A2 .

16
[ 148625-35-8 ]
[ 850074-02-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4562 - 4567.
[2]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4562 - 4567.
[3]Patent: WO2005/34880,2005,A2 .

17
[ 148625-35-8 ]
C₃₅H₂₆N₂SO₃ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4562 - 4567.
[2]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4562 - 4567.

18
[ 148625-35-8 ]
benzo[b]thiophene-2,5-dicarboxylic acid 2-hydroxyamide 5-phenylamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4562 - 4567.
[2]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4562 - 4567.

19
[ 148625-35-8 ]
C₃₆H₂₈N₂SO₃ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4562 - 4567.
[2]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4562 - 4567.

20
[ 148625-35-8 ]
benzo[b]thiophene-2,5-dicarboxylic acid 5-benzylamide 2-hydroxyamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4562 - 4567.
[2]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4562 - 4567.
[3]Patent: WO2005/34880,2005,A2 .

21
[ 148625-35-8 ]
[ 861631-69-8 ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 1341 - 1346.

22
[ 148625-35-8 ]
[ 886853-77-6 ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 1341 - 1346.
[2]Tetrahedron Letters,2011,vol. 52,p. 1815 - 1818.
[3]Patent: US2010/249127,2010,A1 .

23
[ 148625-35-8 ]
[ 886853-95-8 ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 1341 - 1346.

24
[ 148625-35-8 ]
[ 886853-94-7 ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 1341 - 1346.

25
[ 148625-35-8 ]
[ 796854-61-0 ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 1341 - 1346.

26
[ 148625-35-8 ]
3-(5-[4-(methanesulfonyl)-1-piperazinyl]methyl}-1H-indol-2-yl)-quinolin-2(1H)-one hydrochloride [ No CAS ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 1341 - 1346.

27
[ 3113-71-1 ]
[ 148625-35-8 ]

References: [1]Chemical Communications,2007,p. 504 - 506.

28
[ 24078-21-5 ]
[ 148625-35-8 ]

Yield	Reaction Conditions	Operation in experiment
		3-Formyl-4-nitro-benzoic acid methyl ester. A solution of 3-methyl-4-nitro-benzoic acid methyl ester (24.99 g, 128.1 mmol) and N,N-dimethylformamide dimethyl acetal (40.0 mL, 300 mmol) was heated at 1400C for 22.5 h. After cooling to rt, the reaction mixture was concentrated and the residue was crystallized from MeOH to give a purple solid. This solid was dissolved in THF (500 mL) and water (500 mL), and sodium periodate (62.62 g, 292.8 mmol) was added followed by additional sodium periodate (15.6 g, 72.9 mmol) two hours later. After stirring at rt for an additional 1 h, the reaction mixture was filtered through Celite washing with EtOAc (2 L). The filtrate was washed with saturated NaHCO3 (600 mL) and the organic layer was dried over Na2SO4. After filtration, the filtrate was concentrated and the residue was passed through a pad of silica gel, washing with CH2Cl2/hexanes (75percent- 100percent). The filtrate was concentrated and dried to give 3-formyl-4-nitro-benzoic acid methyl ester as yellowish solid. MS (EI): cal'd 210.0 (MH+), exp 210.2 (MH+).
		With a stirrer,A thermometer and a dropping funnel were charged in a 2L three-necked flask35 g of 2,4-dimethylnitrobenzeneAnd 4 g of tetrabutylammonium bromide,And 1000 mL of distilled water was added,Into the water bath,Heated to 90 ,Start the agitator to 300r / min speed stirring;During the stirring,And 85 g of potassium permanganate was added in three portions,After stirring for 1 h,The filtrate was immediately separated by filtration,And the pH was adjusted to 3 with a sulfuric acid solution having a mass concentration of 30percentInto the Buchner funnel,Washed with deionized water and then filtered three times to obtain solid powder; A 2 L three-necked flask equipped with a mechanical stirrer was charged with 70 g of the above separated solid powderAnd 700mL concentration of 40percent methanol solution,Into the water bath,Was heated to 90 20min after dissolution was slowly added dropwise by pipette 50mL concentration of 0.2mol / L sulfuric acid solution,Dropping speed control so that the drop is completed within 30min,Reflux reaction 2h after filtration,Washing and drying to obtain light yellow crystal;50 g of the light yellow crystals obtained above were placed in a stoppered Erlenmeyer flask,10 g of potassium permanganate was added,And then the mixture into the water bath,Heating to 40 degrees Celsius,Stirring with a glass rod for 10 minutes to obtain a mixed liquid;To the above mixture, 20 mL of an acetic acid solution having a mass concentration of 30percent was addedAnd 3 g iron powder,Into the ultrasonic oscillator,Ultrasonic vibration reaction 30min,Ultrasonic power of 100W,Ultrasound frequency of 25KHz,After the end of the ultrasound, the reaction solution was extracted with n-hexane,The organic phase was separated,Into a distillation device,Heated to 85 ° C,After the removal of n-hexane by distillationTo give methyl 3-aldehyde-4-nitrobenzoate.

References: [1]Chemical Communications,2007,p. 504 - 506.
[2]Tetrahedron Letters,1994,vol. 35,p. 219 - 222.
[3]Patent: WO2007/87130,2007,A2 .Location in patent: Page/Page column 70.
[4]Patent: CN105753708,2016,A .Location in patent: Paragraph 0003; 0006.
[5]Patent: WO2006/115845,2006,A1 .
[6]Patent: WO2005/34880,2005,A2 .

29
[ 148625-35-8 ]
4-amino-3-[1,3]dioxolan-2-yl-benzoic acid methyl ester [ No CAS ]

References: [1]Chemical Communications,2007,p. 504 - 506.

30
[ 148625-35-8 ]
[ 929897-34-7 ]

References: [1]Chemical Communications,2007,p. 504 - 506.

31
[ 148625-35-8 ]
[ 929897-20-1 ]

References: [1]Chemical Communications,2007,p. 504 - 506.

32
[ 148625-35-8 ]
[ 929897-35-8 ]

References: [1]Chemical Communications,2007,p. 504 - 506.

33
[ 148625-35-8 ]
(2R,3aR,4R,9bR)-1,5-di-(tert-butoxycarbonyl)-8-methoxycarbonyl-4-[3-(benzyloxy)propyl]-2-(hydroxymethyl)-2,3,3a,4-tetrahydro-9bH-pyrrolo[3,2-c]quinoline [ No CAS ]

References: [1]Chemical Communications,2007,p. 504 - 506.

34
[ 148625-35-8 ]
methyl-4-(tert-butylcarbonylamino)-3-[(6R)-2,2,11,11,12,12-hexamethyl-3,3-diphenyl-4,10-dioxa-3,11-disilatridec-8-en-6-ylimino]methyl}benzoate [ No CAS ]

References: [1]Chemical Communications,2007,p. 504 - 506.

35
[ 148625-35-8 ]
methyl-4-(tert-butylcarbonylamino)-3-{(E)-[(6R,Z)-2,2,11,11,12,12-hexamethyl-3,3-diphenyl-4,10-dioxa-3,11-disilatridec-8-en-6-ylimino]methyl}benzoate [ No CAS ]

References: [1]Chemical Communications,2007,p. 504 - 506.

Historical Records

Technical Information

• Acyl Group Substitution • Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bouveault-Blanc Reduction • Bucherer-Bergs Reaction • Catalytic Hydrogenation • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Ester Cleavage • Fischer Indole Synthesis • Friedel-Crafts Reaction • Grignard Reaction • Hantzsch Dihydropyridine Synthesis • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Julia-Kocienski Olefination • Knoevenagel Condensation • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mukaiyama Aldol Reaction • Nozaki-Hiyama-Kishi Reaction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions with Organometallic Reagents • Reformatsky Reaction • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Stetter Reaction • Stobbe Condensation • Tebbe Olefination • Ugi Reaction • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction

Related Functional Groups of
[ 148625-35-8 ]

Aryls

A151183 [20587-30-8]

Methyl 5-methyl-2-nitrobenzoate

Similarity: 0.98

A152423 [61940-22-5]

Methyl 2-methyl-6-nitrobenzoate

Similarity: 0.98

A297798 [153813-69-5]

Methyl 4-formyl-3-nitrobenzoate

Similarity: 0.98

A435238 [35998-96-0]

Methyl 5-amino-2-nitrobenzoate

Similarity: 0.98

A526900 [84228-45-5]

Methyl 4-amino-2-nitrobenzoate

Similarity: 0.98

Aldehydes

A297798 [153813-69-5]

Methyl 4-formyl-3-nitrobenzoate

Similarity: 0.98

A107781 [138229-59-1]

Methyl 3-formyl-2-nitrobenzoate

Similarity: 0.95

A588841 [90151-04-5]

4-Hydroxy-2-nitrobenzaldehyde

Similarity: 0.82

A221916 [73635-75-3]

4,5-Dihydroxy-2-nitrobenzaldehyde

Similarity: 0.80

A149397 [5858-28-6]

5-Methyl-2-nitrobenzaldehyde

Similarity: 0.79

Esters

A151183 [20587-30-8]

Methyl 5-methyl-2-nitrobenzoate

Similarity: 0.98

A152423 [61940-22-5]

Methyl 2-methyl-6-nitrobenzoate

Similarity: 0.98

A297798 [153813-69-5]

Methyl 4-formyl-3-nitrobenzoate

Similarity: 0.98

A435238 [35998-96-0]

Methyl 5-amino-2-nitrobenzoate

Similarity: 0.98

A526900 [84228-45-5]

Methyl 4-amino-2-nitrobenzoate

Similarity: 0.98

Nitroes

A151183 [20587-30-8]

Methyl 5-methyl-2-nitrobenzoate

Similarity: 0.98

A152423 [61940-22-5]

Methyl 2-methyl-6-nitrobenzoate

Similarity: 0.98

A297798 [153813-69-5]

Methyl 4-formyl-3-nitrobenzoate

Similarity: 0.98

A435238 [35998-96-0]

Methyl 5-amino-2-nitrobenzoate

Similarity: 0.98

A526900 [84228-45-5]

Methyl 4-amino-2-nitrobenzoate

Similarity: 0.98

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CAS No.: 148625-35-8

{[proInfo.proName]}

CAS No.: 148625-35-8

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CAS No.: 148625-35-8

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Medicinal Chemistry

Application In Synthesis of [ 148625-35-8 ]

[ 148625-35-8 ] Synthesis Path-Downstream 1~35

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Related Functional Groups of [ 148625-35-8 ]

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