37901-90-9|3-Amino-4-methyl-2-nitrobenzoic acid| Ambeed

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Quality Control of [ 37901-90-9 ] Purity: 95% SDS Specification

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Product Details of [ 37901-90-9 ]

CAS No. :	37901-90-9
Formula :	C₈H₈N₂O₄
M.W :	196.16
SMILES Code :	O=C(O)C1=CC=C(C)C(N)=C1[N+]([O-])=O
MDL No. :	MFCD01098202
InChI Key :	JLWAVVAJFWDXEF-UHFFFAOYSA-N
Pubchem ID :	5077335

Safety of [ 37901-90-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Application In Synthesis of [ 37901-90-9 ]

* 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 [ 37901-90-9 ]

[ 37901-90-9 ] Synthesis Path-Downstream 1~30

2
[ 37901-90-9 ]
[ 745048-56-0 ]

Yield	Reaction Conditions	Operation in experiment
85%	With formic acid;palladium 10% on activated carbon; In water; for 15h;Heating / reflux;	Preparation of 7-Methyl-1H-benzimidazole-4-carboxylic Acid (22) A mixture of <strong>[37901-90-9]3-amino-4-methyl-2-nitrobenzoic acid</strong> (16) ((16) (6.883 g, 35.10 mmol), 10% Pd/C [0.3 g, 10% dry Pd/C] and 75% aqueous formic acid (60 ML) is heated to reflux for about 15 hours. to give 7-Methyl-1H-benzimidazole-4-carboxylic Acid (22)22), as beige solid (5.26 g, 85% Yield).

References: [1]Patent: US2004/167194,2004,A1 .Location in patent: Page 23.

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[ 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.

4
[ 37901-90-9 ]
[ 882679-22-3 ]

Yield	Reaction Conditions	Operation in experiment
84%		Example 44 Preparation of 3-iodo-4-methyI-2-nitrobenzoic acid3-Atnino-4-methyI-2-nitrobenzoic acid (13 g, 66 mmol) was taken up in 50 mL of DMSO and 30% aqueous sulfuric acid (150 mL) was added. The mixture was cooled to 0 0C and sodium nitrite (7 g, 99 mmol) dissolved in 20 mL of water was added slowly. The mixture was stirred for 1 h and potassium iodide (28 g, 166 mmol) dissolved in 50 mL of water was added. The mixture was allowed to stir at RT for 1 h. The mixture was extracted with ethyl acetate and the organic layer washed with an aqueous solution of 2 M sodium sulfite, water and brine. The organic layer was dried with sodium sulfate and concentrated under vacuum to give 3-iodo-4-methyl~2-nitrobenzoic acid (17 g, 84%) as a light brown solid. MS (M+H)+ 308.
70%		To a solution of 5D (4 g, 20.4 mmol) in DMSO (40 mL) in an ice-water bath, was added H2S04 (30%, 40 mL) slowly followed by slow addition of NaN02 (2.11 g, 30.6 mmol) in water (10 mL). The resulting mixture was stirred in ice-water bath for lh. KI (8.47 g, 51 mmol) in water (20 mL) was added slowly to the reaction mixture and the resulting mixture was stirred at RT for 16 h. The mixture was extracted with ethyl acetate and washed with brine. The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel to afford the desired product 5E (4.3 g, 70%). ESI-MS m/z: 308 [M+H]+.

References: [1]Patent: WO2007/76092,2007,A2 .Location in patent: Page/Page column 72.
[2]Patent: WO2018/218070,2018,A2 .Location in patent: Page/Page column 181; 182.

5
[ 2458-12-0 ]
[ 37901-90-9 ]

References: [1]Patent: WO2015/27222,2015,A2 .
[2]Patent: WO2018/218070,2018,A2 .

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[ 6946-14-1 ]
[ 37901-90-9 ]

References: [1]Patent: WO2015/27222,2015,A2 .
[2]Patent: WO2018/218070,2018,A2 .

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[ 37901-90-9 ]
[ 320740-32-7 ]