Trifluoroacetic acid → 4-Amino-3-hydroxybenzonitrile

Participants

Reaction Steps

To a solution of N-t-butylacetoxy-4-cyano-2-hydroxyl aniline (3.1 g, 13 mmol) in methylene chloride (100 mL) at 0° C. was added trifluoroacetic acid and the reaction mixture was allowed to warm to rt. After 2.5 h, the reaction was quenched with water (100 mL) and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crude material was purified by flash column chromatography (50% ethyl acetate/hexanes) to give 1.7 g (96%) of 4-cyano-2-hydroxyl aniline as a tan solid. 1H NMR (400 MHz, DMSO) δ 7.0 (d, 1H), 6.85 (s, 1H), 6.65 (d, 1H); MS(EI) m/e 134 (M+).

Provenance & Evidence