Sodium Hydroxide → (+/-)-4-(4,4,4-Trifluoro-1-(quinolin-3-ylamino)butyl)benzoic acid

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Reaction Steps

To a solution of ethyl(+/−)-4-(4,4,4-trifluoro-1-(quinolin-3-ylamino)butyl)benzoate (95 mg, 0.24 mmol) in methanol (1.2 mL) and tetrahydrofuran (1.2 mL) was added 1 N aq sodium hydroxide (1.2 mL, 1.2 mmol). After 17 hours, the solution was concentrated under reduced pressure to remove methanol and tetrahydrofuran. The mixture was then acidified to pH 5 with 1 N aq hydrochloric acid and diluted with sat. aq sodium chloride (20 mL). The mixture was extracted with ethyl acetate (3×20 mL). The combined organic layers were dried over Na2SO4 and filtered, and the filtrate was concentrated under reduced pressure to give (+/−)-4-(4,4,4-trifluoro-1-(quinolin-3-ylamino)butyl)benzoic acid. 1HNMR (400 MHz, CD3OD) δ 8.50 (br. s, 1H), 8.02 (d, J=8.2 Hz, 2H), 7.80-7.73 (m, 1H), 7.57 (d, J=8.2 Hz, 2H), 7.53-7.47 (m, 1H), 7.40-7.32 (m, 2H), 6.95 (d, J=2.5 Hz, 1H), 4.73-4.64 (m, 1H), 2.55-2.39 (m, 1H), 2.39-2.22 (m, 1H), 2.22-2.04 (m, 2H).

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