Ammonia → HCID 67930020, compound

Participants

Reaction Steps

A solution of 4'-methoxy-3'-methylacetanilide (71g) in dry tetrahydrofuran (350 ml) was added over 45 minutes to a stirred suspension of sodium hydride (19 g of a 50% dispersion in mineral oil) in dry tetrahydrofuran (250 ml) under nitrogen. The stirred mixture was heated under reflux for 10 minutes, then cooled to 0 to 5° and iodomethane (25 ml) added dropwise over 10 minutes. After the mixture was stirred and heated under reflux for a further 2 hours, the mixture was cooled to ambient temperature and industrial methylated spirit (50 ml) followed by aqueous ammonia (specific gravity 0.88, 50 ml) were added. After 30 minutes, solvent was removed by evaporation, water (500 ml) added to the residue and the mixture extracted with ethyl acetate (3×300 ml). The combined extracts were washed with aqueous sodium metabisulphite (10% w/w, 2×300 ml), dried over magnesium sulphate, and the solvent removed by evaporation. The residue was triturated with petroleum ether (b.p. 40°-60° ) and the solid collected by filtration to give the novel compound 4'-methoxy-3'-methyl-N-methylacetanilide, m.p. 65°-66°.

Provenance & Evidence