Methanol → HCID 21422780, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 32.5 g of m-(N-methyl-N-methoxy-carbamoyloxy)-acetylacetanilide, 0.4 g of p-toluene sulfonic acid, 32.5 g of methyl orthoformate and 60 ml of methanol was stirred for 24 hours at 20°C and after the addition of 0.4 g of quinoline, the mixture was evaporated to dryness to obtain 40 g of m-(N-methyl-N-methoxy-carbamoyloxy)-3,3-dimethoxy-butyranilide. The product was dissolved in 175 ml of toluene and the solution was heated at 140°C. for 5 hours while distilling off a toluene-methanol azeotrope. The mixture was then evaporated to dryness and the residue was chromatographed over silica gel. Elution with a 9-1 methylene chloride-acetone mixture yielded 11.5 g of m-(N-methoxy-carbamoyloxy)-3-methoxy-crotonanilide with a refractive index nD20 = 1.544.

Provenance & Evidence