5-((3-Benzyloxy-4-methoxyanilino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione → 7-(Benzyloxy)-6-methoxyquinolin-4-ol

Participants

Reaction Conditions

Reaction Steps

5-((3-Benzyloxy-4-methoxyanilino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (10 g, 26 mmol) was rapidly added to phenyl ether (150 ml) heated at reflux. The mixture maintained a vigorous reflux for 5 minutes, and was allowed to cool to 45° C. then poured into petroleum ether. The resulting solid was collected by filtration and purified by column chromatography eluting with methylene chloride/methanol (95/5 followed by 90/10 and 85/5) to give 7-benzyloxy-6-methoxy-1,4-dihydroquinolin-4-one (6 g, 82%) as a yellow solid.

Provenance & Evidence