Lithium Hydroxide → 3-(Quinolin-6-yl)propanoic acid

Participants

Reaction Steps

To a solution of 3-quinolin-6-yl-propionic acid ethyl ester (100 mg, 0.437 mmol) in methanol (2 mL) was added 4 M aqueous solution of lithium hydroxide (0.55 mL, 2.18 mmol). The reaction mixture was stirred at room temperature for 3 h then it was concentrated in vacuo, diluted with water, and treated with 1 N aqueous hydrochloric acid until pH 5. The aqueous layer was extracted with ethyl acetate (3×), and the combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to provide 18 mg of product as a white solid. 1H NMR 500 MHz (DMSO) δ 2.67 (t, 2H), 3.02 (t, 2H), 7.50 (dd, 1H), 7.67 (dd, 1H), 7.78 (d, 1H), 7.94 (d, 1H), 8.29 (dd, 1H), 8.84 (dd, 1H); MS (m/z) 202 [M+H+]+.

Provenance & Evidence