Ethyl Acetate → 3-Chloro-5-fluoro-6-methoxy-quinoline-4-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

Selectfluor (2.4 g, 6.77 mmol, 1.5 eq) is added at 10° C. to a stirred solution of 3-chloro-6-methoxy-quinoline-4-carbaldehyde (1.0 g, 4.5 mmol, 1.0 eq) in acetonitrile (50 mL). After 24 hours stirring at 10° C., the reaction mixture is extracted with ethyl acetate (3×100 mL) and brine (50 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a crude product that is purified by column chromatography (silica gel, eluent: petroleum ether:ethyl acetate, 10:1 to 5:1, v/v) to afford 3-chloro-5-fluoro-6-methoxy-quinoline-4-carbaldehyde as a yellow solid (620 mg, 57% yield).

Provenance & Evidence