N-(3-methylphenyl)-3-oxobutanamide → HCID 70633462, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 80 g of N-(m-tolyl)-acetoacetamide, 80 g of methyl orthoformate, 100 ml of methanol and 1 g of p-toluene sulfonic acid was refluxed with stirring for 6 hours and the volatile material was distilled off under reduced pressure. 300 ml of toluene and 1.5 ml of quinoline were added and the mixture was heated to about 140° C for 3 hours and then the rest of the toluene was evaporated. The residue was chromatographed over silica gel with a mixture of 9-1 methylene chloride-ethyl acetate as eluant to obtain 40 g of N-(m-tolyl)-3-methoxy-crotonamide melting at 106° C.

Provenance & Evidence