2-(Benzoyloxymethyl)phenylaminoacrylate → 4-Hydroxyquinoline

Participants

Reaction Steps

Diphenyl ether (500 ml) was heated to reflux, ethyl 2-isobutyryl-3-(2-(benzoyloxymethyl)phenylaminoacrylate (29.3 g, 74.1 mmol) added, and heating continued for 15 minutes. The bulk of the diphenyl ether was removed by vacuum distillation, and the residue chromatographed (silica gal, 1%-2.5% methanol in dichloromethane) and recrystallized from ethyl acetate to give 3-isobutyryl-8-benzoyloxymethyl)-4(1H)-quinolone (11.9 g, 46%), m.p. 158°-160°.

Provenance & Evidence