N-(2-Bromophenyl)cinnamamide → 8-Bromo-1,2-dihydroquinolin-2-one

Participants

Reaction Conditions

Reaction Steps

A mixture of N-(2-bromophenyl)cinnamamide (172.3 g, 570.3 mmol), aluminum chloride (456 g, 342 mmol) and chlorobenzene (1000 ml) were allowed to stir at 100° C. for 7 hours followed by cooling to ambient temperature overnight. The resulting mixture was poured onto 2 kg of ice and was allowed to warm to ambient temperature over 1 hour. The resulting mixture was extracted with dichloromethane. The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. The resulting solids were triturated with 1000 ml hexanes. The solids were vacuum dried to yield title compound. (83 g, 65% yield) MS ESI (+) m/z 224 and 226 (M+1 of each isotope) detected.

Provenance & Evidence