m-Chloroperbenzoic acid → 8-Fluoro-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl acetate

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Reaction Steps

To a stirring solution of 6-acetyl-8-fluoro-3,4-dihydroquinolin-2(1H)-one (1.6 g, 7.72 mmol) in CHCl3 (100 mL) at room temperature was added in portions m-chloroperbenzoic acid (2.077 g, 9.27 mmol). The reaction mixture was stirred at reflux for 18 h, then cooled to room temperature and quenched with saturated sodium bicarbonate solution. The reaction was extracted with DCM (3×100 mL). The combined organic layers were dried over MgSO4 and concentrated under vacuum to a yellow oil. This was purified by column chromatography on silica gel using 1% MeOH in DCM to give 8-fluoro-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl acetate as a white foam (1.3 g, 75%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.28 (s, 1H), 6.84-6.72 (m, 1H), 2.77-2.54 (m, 2H), 2.45-2.21 (m, 2H), 1.62 (s, 3H). LCMS: R.T.=1.382 min; [M+H]+=224.0.

Provenance & Evidence