2-Amino-5-cyanobenzoic acid

159847-81-1

99767-45-0

General procedure for the synthesis of 2-amino-5-cyanobenzoic acid from methyl 2-amino-5-cyanobenzoate: to a methanolic (200 mL) suspension of methyl 2-amino-5-cyanobenzoate (9.55 g, 54.2 mmol) was added an aqueous sodium hydroxide solution (30 mL, 6.0 M, 180 mmol). The reaction mixture was stirred at room temperature and a homogeneous solution was formed after 1 hour. After 27.5 hours of reaction, the solvent was removed by evaporation under reduced pressure and the residue was dissolved in water (300 mL). The resulting aqueous phase was washed with dichloromethane (2 x 200 mL) and subsequently acidified to acidity with concentrated hydrochloric acid (1 L). The product was extracted with ethyl acetate (500 mL), the organic phases were combined and dried over anhydrous magnesium sulfate. The organic phase was concentrated under reduced pressure to give 8.57 g (97.5% yield) of yellow solid product, which could be used in subsequent reactions without further purification.