Hydrochloric Acid → 2-Amino-5-nitro-4-trifluoromethyl-benzoic acid

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Reaction Conditions

Reaction Steps

To a solution of 490 mg (1.85 mmol) of 2-amino-5-nitro-4-trifluoromethyl-benzoic acid methyl ester in 5 ml methanol, 4.7 ml (9.27 mmol) of 2 M sodium hydroxide solution is added. The yellow solution is stirred at 60° C. for 12 hours. Subsequently hydrochloric acid (1M) is added to adjust to pH=2. The solvent volume is reduced by evaporation and is extracted with ethyl acetate. The organic layers are combined, dried and the solvent is evaporated to yield 2-amino-5-nitro-4-trifluoromethyl-benzoic acid. 1H-NMR; DMSO-d6 (400 MHz, ppm): 8.58 (s, 1H, aromatic); 8.10 (s(broad), 2H, NH2); 7.35 (s, 1H, aromatic).; LC-MS: 249 [M-H]- ; Agilent LC/MSD 1100 Series; LC-MS method: Column: SunFireCl8, 4.6*50 mm, 3.5 μm; negative MS; water/acetonitril 95:5 to 5:95 in 5 min, flow: 1.5 ml/min.

Provenance & Evidence