Sodium Hydroxide → 2-(Trifluoromethyl)-5,6,7,8-tetrahydroquinoline-6-carboxylic acid

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Reaction Conditions

Reaction Steps

A 25 mL flask was charged with methyl 2-(trifluoromethyl)-5,6,7,8-tetrahydroquinoline-6-carboxylate (6 mg, 0.02 mmol), methanol (3 mL) and 1 M aqueous sodium hydroxide (0.23 mL, 10 equiv), and the mixture heated in an oil bath at 90° C. The mixture was removed from the heat after 1.5 h, diluted with 1M NaH2PO4 (10 mL), buffered to pH 3 with 1M H3PO4, then extracted with DCM (3×20 mL). The combined organic extracts were dried (Na2SO4), filtered, and concentrated to afford the acid as a white solid (6 mg, 100%). 1H NMR (400 MHz, CDCl3) δ 7.59 (d, J=8.0 Hz, 1H), 7.46 (d, J=8.0 Hz, 1H), 3.21-3.02 (m, 4H), 2.95-2.84 (m, 1H), 2.42-2.32 (m, 1H), 2.14-2.03 (m, 1H), 1.10 (br s, 11-1); m/z=246.4 (M+H)f.

Provenance & Evidence