3-Butyryl-4-chloro-8-methoxyquinoline → 1-[4-(4,6-Dimethyl-benzo[1,3]dioxol-5-ylamino)-8-methoxy-quinolin-3-yl]-butan-1-one

Participants

Reaction Steps

2,6-Dimethyl-3,4-(methylenedioxy)aniline (1.67 g, 20 mmol) and 3-butyryl-4-chloro-8-methoxyquinoline (2.3 g, 10 mmol) were heated together under reflux in 1,4-dioxan (50 ml) for 2 hours. The solvent was evaporated and the residue was dissolved in dichloromethane, washed with 2M HCl, sodium hydrogen carbonate solution (×2) and brine. The organic solution was dried, filtered and evaporated to a solid which was recrystallized from ethanol to give 3-butyryl-4-(3,4-methylenedioxy-2,6-dimethylphenylamino)-8-methoxyquinoline (17 g, 43%), m.p. 150°-2° C.

Provenance & Evidence