Benzoic acid, 2-amino-3-nitro-, methyl ester
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Benzoic acid, 2-amino-3-nitro-, methyl ester
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CAS No:
57113-91-4
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Formula:
C8H8N2O4
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Chemical Name:
Benzoic acid, 2-amino-3-nitro-, methyl ester
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Synonyms:
Benzoic acid,2-amino-3-nitro-,methyl ester;Anthranilic acid,3-nitro-,methyl ester;Methyl 3-nitroanthranilate;Methyl 2-Amino-3-nitrobenzoate;2-Amino-3-nitrobenzoic acid methyl ester
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CAS No:
Benzoic acid, 2-amino-3-nitro-, methyl ester Basic Attributes
196.16
196.16
1312995-182-4
DTXSID30345810
2922499990
Safety Information
36/37/38-22
26-36/37/39
Xi,Xn
Irritant
P264, P270, P280, P301+P312, P302+P352, P305+P351+P338, P321, P330, P332+P313, P337+P313, P362, P501
H302
|Warning|H302 (92.68%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 41 companies from 4 notifications to the ECHA C&L Inventory.
Benzoic acid, 2-amino-3-nitro-, methyl ester Use and Manufacturing
After dissolving 2-amino-3-nitrobenzoic acid (1.00 g, 5.49 mmol) in methanol (40 ml), sulfuric acid (0.50 ml) was added and the mixture was heated to reflux for 2 days. The reaction mixture was cooled to room temperature, and then the pH was adjusted to approximately 9 with saturated aqueous sodium bicarbonate and the mixture was concentrated under reduced pressure to approximately 10 ml. Water (20 ml) was added, the mixture was extracted with ethyl acetate (10 ml x 3 times), and the obtained organic layer was dried over anhydrous magnesium sulfate. It was then concentrated under reduced pressure, and the produced crystals were dried to obtain 2-amino-3-nitrobenzoic acid methyl ester. The compound was identified by NMR. Yield: 661.4 mg (61percent).1H-NMR (270 MHz, CDCl3): δ8.50(br), 8.37(1H, dd, J=8.6, 1.4 Hz), 8.23(1H, dd, J=7.6, 1.4 Hz), 6.65(1H, dd, J=8.6, 7.6Hz), 3.92(3H, s) ppm.(Preparation 21) (0103) 1) A mixture of methyl ester of 2-acetoamino-3-nitrobenzoic acid (1.444 g, 6.06 mmol) and 6N hydrochloric acid (30 ml) was heated under reflux for 15 min. The reaction mixture was cooled with ice, adjusted to pH 8 with 10percent aqueous solution of potassium carbonate and then extracted with ethyl acetate. The extract was washed with water and brine in turn and dried. The solvent was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=1) to give methyl ester of 2-amino-3-nitrobenzoic acid (987 mg, 83percent) as yellow crystals. m.p.: 94-96° C.; APCI-MS m/z: 197 [M+H](III) LiOH (7.6 g) was added to a solution of the product just obtained in stage (II) (30 g) in THF (450 ml) and the mixture was stirred at room temperature for 1 h. Dimethyl sulfate (17.25 ml) was then added and the mixture was heated under reflux for 24 h. The reaction mixture was cooled to room temperature and filtered and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and the solution was washed with NH
An intermediate in the preparation of Candesartan.
Computed Properties
Molecular Weight:196.16
XLogP3:1.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:2
Exact Mass:196.04840674
Monoisotopic Mass:196.04840674
Topological Polar Surface Area:98.1
Heavy Atom Count:14
Complexity:238
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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Benzoic acid, 2-amino-3-nitro-, methyl ester
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