HCID 67403309, compound → Benzoic acid, 5-amino-4-cyano-2-fluoro-, methyl ester

Participants

Reaction Steps

To a solution of methyl 4-cyano-2-fluoro-5-nitrobenzoate (785 mg, 3.5 mmol) in acetic acid (15 mL) was added iron powder (1.17 g, 21.0 mmol). The mixture was stirred vigorously at room temperature for 2 h. Insoluble solids were then removed by filtration through celite. Water was added to the filtrate and the aqueous mixture was extracted with ethyl acetate. The organic extract was washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and concentrated. The residue was purified by column chromatography (30% ethyl acetate in hexanes) to provide methyl 5-amino-4-cyano-2-fluorobenzoate (463 mg, 2.38 mmol, 68% yield). 1H NMR (400 MHz, CDCl3): 7.30 (d, 1H), 7.19 (d, 1H), 4.41 (br s, 2H), 3.94 (s, 3H); MS (EI) for C9H7FN2O2: 193 (M−H).

Provenance & Evidence