Trifluoroacetic acid → 2-(Trifluoromethyl)quinoline-6-carboxylic acid

Participants

Reaction Steps

To a solution of tert-butyl 2-trifluoromethylquinoline-6-carboxylate (2 g, 7 mmol) in dichloromethane (50 mL), cooled to 0° C., was added trifluoroacetic acid (5.18 mL, 67.2 mmol) and the reaction mixture allowed to warm to room temperature and stirred for 36 h. The reaction mixture was concentrated under reduced pressure and the crude product obtained triturated with heptane (4×10 mL) to give 2-trifluoromethylquinoline-6-carboxylic acid (1.58 g, 98%). 1H NMR (400 MHz, CD3OD) δ 7.93 (1H, d), 8.24 (1H, d), 8.42 (1H, dd), 8.73 (1H, d), 8.78 (1H, d). LCMS: Retention time: 1.38 min. MS (ESI) m/z 242 (M+H)+.

Provenance & Evidence