Sodium Hydroxide → 2-Tert-butylquinoline-6-carboxylic acid

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Reaction Steps

To a solution of methyl 2-tert-butylquinoline-6-carboxylate (347 mg, 1.43 mmol) in methanol (4 ml) and THF (4 ml) was added 2N aqueous sodium hydroxide (2 ml) at room temperature. The mixture was stirred at room temperature for 1.5 hours, then evaporated, diluted with water (5 ml), and neutralized to pH 5˜6 by 2M aqueous hydrochloride. The formed precipitate was collected and washed with water to furnish the title compound (282 mg, 86% yield) as a white solid. 1H NMR (300 MHz, CDCl3) δ1.49 (9H, s), 7.62 (1H, d, J=8.8 Hz), 8.13 (1H, d, J=8.8 Hz), 8.20 (1H, d, J=8.8 Hz), 8.31-8.34 (1H, m), 8.64-8.66 (1H, m). MS (ESI): m/z 230 (M+H)+.

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