7356-52-7|3-Acetamido-4-methyl-2-nitrobenzoic acid| Ambeed

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Quality Control of [ 7356-52-7 ] Purity: 97% SDS Specification

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Product Details of [ 7356-52-7 ]

CAS No. :	7356-52-7
Formula :	C₁₀H₁₀N₂O₅
M.W :	238.20
SMILES Code :	C1=C(C(=C(C(=C1)C)NC(C)=O)[N+](=O)[O-])C(O)=O
MDL No. :	MFCD00755098
Boiling Point :	No data available
InChI Key :	TXVWKWQKCFPEDJ-UHFFFAOYSA-N
Pubchem ID :	243433

Safety of [ 7356-52-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H317
Precautionary Statements:	P280

Computational Chemistry of [ 7356-52-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	17
Num. arom. heavy atoms	6
Fraction Csp3	0.2
Num. rotatable bonds	4
Num. H-bond acceptors	5.0
Num. H-bond donors	2.0
Molar Refractivity	61.5
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	112.22 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.07
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	1.37
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.37
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.	0.44
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	-0.8
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.69

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.18
Solubility	1.58 mg/ml ; 0.00665 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.	-3.33
Solubility	0.112 mg/ml ; 0.000468 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	-1.93
Solubility	2.77 mg/ml ; 0.0116 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.	-6.78 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.	0.56

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	2.0 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)	2.42

Application In Synthesis of [ 7356-52-7 ]

* 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 [ 7356-52-7 ]

[ 7356-52-7 ] Synthesis Path-Downstream 1~35

2
[ 6946-14-1 ]
[ 6632-23-1 ]
[ 7356-52-7 ]

References: [1]Tetrahedron,2000,vol. 56,p. 8735 - 8746.

3
[ 7356-52-7 ]
3-amino-4-methyl-2-nitrobenzoic acid hydrobromide [ No CAS ]

References: [1]Tetrahedron,2000,vol. 56,p. 8735 - 8746.

4
[ 7356-52-7 ]
[ 6946-15-2 ]

Yield	Reaction Conditions	Operation in experiment
93.4%		A solution of <strong>[7356-52-7]3-(acetylamino)-4-methyl-2-nitrobenzoic acid</strong> (237.5 g, 0.997 mol) and KOH (451.2 g, 8.04 mol) in water (2830 mL) was refluxed for 48 h. The dark red solution was cooled and acidified to pH 1 with concentrated HCI. The yellow solid was filtered and re-crystallized from water (1800 mL) to give the title compound (183 g, 93.4%) as a yellow solid.

References: [1]Patent: WO2007/125405,2007,A2 .Location in patent: Page/Page column 27; 87.

5
[ 2458-12-0 ]
[ 7356-52-7 ]

References: [1]Tetrahedron,2000,vol. 56,p. 8735 - 8746.
[2]Patent: WO2015/27222,2015,A2 .
[3]Patent: WO2018/218070,2018,A2 .

6
[ 7356-52-7 ]
[ 20587-29-5 ]

References: [1]Tetrahedron,2000,vol. 56,p. 8735 - 8746.

7
[ 7356-52-7 ]
[ 320740-34-9 ]

References: [1]Tetrahedron,2000,vol. 56,p. 8735 - 8746.

8
[ 7356-52-7 ]
2-amino-3-bromo-4-methylbenzoic acid [ No CAS ]

References: [1]Tetrahedron,2000,vol. 56,p. 8735 - 8746.
[2]Patent: WO2015/27222,2015,A2 .

9
[ 7356-52-7 ]
[ 320740-33-8 ]

References: [1]Tetrahedron,2000,vol. 56,p. 8735 - 8746.

10
[ 7356-52-7 ]
[ 320740-32-7 ]

References: [1]Tetrahedron,2000,vol. 56,p. 8735 - 8746.
[2]Patent: WO2015/27222,2015,A2 .

11
[ 7356-52-7 ]
2,2'-dinitro-6,6'-dimethyl-3,3'-dimethoxycarbonylbiphenyl [ No CAS ]

References: [1]Tetrahedron,2000,vol. 56,p. 8735 - 8746.

12
[ 6946-14-1 ]
[ 7356-52-7 ]

Yield	Reaction Conditions	Operation in experiment
77%	With nitric acid; In water; for 2.5h;	To a solution of HN03 (47 mL, 98%) in ice-water, was added 3-acetamido-4- methylbenzoic acid (11.6 g, 60 mmol) in portions over lh and the resulting mixture was stirred in ice-water for 1.5 h. Then ice was added slowly and the mixture was stirred for 0.5 h. The resulting precipitate was collected by filtration and dried to afford the desired product 5C (11 g, 77%). ESI-MS m/z: 239 [M+H]+.
63%		Example 42 Preparation of 3-acetamido-4-methyl-2-nitrobenzoic acid3-Acetamido-4-methylbenzoic acid (205 g, 1061 mmol) was added portionwise over 45 min to stirred fuming nitric acid (1 L) at -5 0C5 maintaining a reaction temperature below 0 0C. The mixture was stirred for an additional 1 h and then crushed ice (2.5 kg) was added. The mixture was stirred for a further 30 min. The precipite that formed was filtered off and thouroughly washed with water. The resulting cake was air dried and suspended in 1 L of acetic acid at 65 0C. The suspension was sitrred for 1 hour, allowed to cool down to RT and then filtered. The filtrate was washed with acetic acid and ether to give 3-acetamido-4-methyl-2-nitrobenzoic acid (160 g, 63%) as a white solid. MS (M+H)+ 239.
54%	With nitric acid; at 0 - 5℃; for 3h;	To a solution of fuming HN03(500 mL) at 0-5 C was added 3-acetamido-4- methylbenzoic acid (123 g, 0.637 mol, 1 eq.) in portions over 1 h. The mixture was stirred for 1.5 h, then ice was added. The mixture was stirred for a further 30 min. The solid was collected by filtration, and dried in vacuo to afford 3-acetamido-4-methyl-2-nitrobenzoic acid (82 g, 54% yield).

51.8%	With nitric acid; at 0 - 5℃; for 2h;	3-(acetylamino)-4-methylbenzoic acid (300 g, 1.55 mol) was added portionwise to fuming nitric acid (1200 mL) with stirring over a period of 1 h at 0~5C. The solution gradually turned into a heavy slurry during the addition. At the end of addition, an additional fuming nitric acid (200 mL) was added. The reaction mixture was stirred for an additional hour at 50C, then allowed to warm to room temperature and poured into ice water. The solid formed was collected and washed with water (450 mLchi3). The crude product was re- crystallized from acetic acid (1800 mL) to give the title compound (191.5 g, 51.8%) as a white solid.
51%	With nitric acid; at 0℃; for 2.5h;	Preparation of 3-(Acetylamino)-4-methyl-2-nitrobenzoic Acid (15): Fuming nitric acid (100 ML, 2.4 mol) is cooled to about 0 C. (ice/acetone/water bath) and 3-(Acetylamino)-4-methylbenzoic Acid (14) (24.567 g, 127.2 mmol) is added in small portions over about 30 minutes, at rate to maintain the internal reaction temperature <5 C. The hetereogeneous reaction mixture is then stirred at about 0 C. for an additional 1 hour.The reaction mixture is then added to ice water (300 ML) and stirred for about 1 hour.The solid obtained is filtered and dried to provide a mixture of 3-N-acetyl-4-methyl-2-nitro benzoic acid (5) and(5) and 3-N-acetyl-4-methyl-5-nitro benzoic acid, in ratio of about 78:22 (27.79 g, 92% Combined Yield).A portion of this mixture (23.458 g) is recrystallized from acetic acid (300 ML) to give 3-(Acetylamino)-4-methyl-2-nitrobenzoic Acid (15)15), as a white solid (15.370 g, 51% yield).

References: [1]Patent: WO2018/218070,2018,A2 .Location in patent: Page/Page column 181; 182.
[2]Patent: WO2007/76092,2007,A2 .Location in patent: Page/Page column 71.
[3]Patent: WO2015/27222,2015,A2 .Location in patent: Paragraph 0278.
[4]Patent: WO2007/125405,2007,A2 .Location in patent: Page/Page column 27; 87.
[5]Patent: US2004/167194,2004,A1 .Location in patent: Page 23.

13
[ 7356-52-7 ]
[ 37901-90-9 ]

Yield	Reaction Conditions	Operation in experiment
93%	With hydrogenchloride; In 1,4-dioxane; water; for 16h;Reflux;	To a solution of 5C (11 g, 49 mmol) in 1,4-dioxane (110 mL) at RT, was added HCl (6N, 200 mmol) slowly and the resulting mixture was stirred at reflux for 16 h. The mixture was concentrated in vacuo. The residue was extracted with ethyl acetate and washed with brine. The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was triturated with PE/EA (10/1) and dried to afford the desired product (9 g, 93%). ESI-MS m/z: 197 [M+H]+.
92.7%	With hydrogenchloride; In 1,4-dioxane;Reflux;	To a solution of 3-acetamido-4-methyl-2-nitrobenzoic acid (79 g, 0.33 mol, 1.0 eq. ) in dioxane (400 mL) was added HCI (6 N, 200 mL) dropwise. The mixture was heated under reflux overnight, then extracted with EA (200 mL X 3). The combined organic phases were dried over Na2S04and concentrated. The solid was triturated with the mixed solvent (PE/EA=10/1, v/v) and filtered to afford 3-amino-4-methyl-2-nitrobenzoic acid (60 g, 92.7% yield).
84%	With hydrogenchloride; water; In 1,4-dioxane; at 80℃; for 16h;	Example 43 Preparation of 3-amino-4-methyl-2-nitrobenzoic acid3-Acetamido-4-methyl-2-nitrobenzoic acid (65 g, 273 mmol) was taken in dioxane (350 mL) and treated with 5 N aqueous HCl (150 mL). The reaction was stirred at 80 0C for 16 h. The dioxane was removed under reduced pressure and the residue poured onto crushed ice. The resulting precipitate was filtered off. The filtrate was extracted with ethyl acetate (2x). The organic layer and the solid were combined and concentrated under vacuum to give 3-amino-4-methyl-2-nitrobenzoic acid (45 g, 84% yield) as a yellow solid. MS (M+H)+ 197.

61%

With sulfuric acid; In water; at 115℃; for 0.5h;

Preparation of 3-Amino-4-methyl-2-nitrobenzoic Acid (16): To a 70% aqueous solution of H2SO4 (100 ML) is added 3-(Acetylamino)-4-methyl-2-nitrobenzoic Acid (15) (14.30 g, 60.00 mmol), and the reaction mixture heated to about 115 C. for about 30 minutes.The mixture is then cooled to ambient temperature, added to ice water (250 ML) and held at about 0 C. for about 30 minutes.The resulting solid is filtered, washed with water (100 ML), and dried to provide 3-amino-4-methyl-2-nitrobenzoic acid (16) as(16) as a rust colored solid (7.17 g, 61% yield).

References: [1]Patent: WO2018/218070,2018,A2 .Location in patent: Page/Page column 181; 182.
[2]Patent: WO2015/27222,2015,A2 .Location in patent: Paragraph 0279.
[3]Patent: WO2007/76092,2007,A2 .Location in patent: Page/Page column 71.
[4]Patent: US2004/167194,2004,A1 .Location in patent: Page 23.

14
[ 7356-52-7 ]
8-bromo-7-methylquinazoline-2,4-diol [ No CAS ]