m-Chloroperbenzoic acid → 8-Bromo-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl acetate

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Reaction Steps

To a solution of 3-acetyl-8-bromo-1-methylquinolin-4(1H)-one (3.4 g, 12.14 mmol) in dichloromethane (60 mL) at room temperature was added portionwise with stirring m-CPBA (4.08 g, 18.21 mmol). The resulting mixture was stirred at room temperature for 1 h. The excess m-CPBA was quenched via addition of 15% aqueous Na2SO3 (30 mL), and the resulting mixture was stirred at room temperature for 0.5 h. The layers were separated, and the organic layer was washed sequentially with water (100 mL), 5% aqueous NaHCO3 (100 mL), and brine (100 mL). The organic layer was dried (Na2SO4), filtered, and concentrated in vacuo to afford crude 8-bromo-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl acetate (3.68 g, 10.56 mmol, 87% yield) as brown solid, which was used in the next hydrolysis step without further purification. LCMS: (M+H)+: 295.9.

Provenance & Evidence