N-methyl-2-oxo-2-phenylacetamide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Hydroxylamine hydrochloride (5.96 g, 2.5 eq.) was added to a solution of N-methyl-2-oxo-2-phenylacetamide (5.6 g, 34.3 mmol) in pyridine (25 ml). After stirring for 10 h at room temperature, the excess pyridine was removed in vacuo and the residue was taken up in 250 ml of dichloromethane. The organic phase was washed with 200 ml of water and then again with aqueous hydrochloric acid (0.1 M, 250 ml). The precipitated solid was filtered off, giving 2-(hydroxyimino)-N-methyl-2-phenylacetamide as a yellow solid (2.31 g, pure Z isomer). The filtrate was concentrated by evaporation in vacuo. This gave 4.50 g of 2-(hydroxyimino)-N-methyl-2-phenylacetamide (Z/E=mixture of isomers) as a yellow solid. the excess pyridine was removed in vacuo The organic phase was washed with 200 ml of water The precipitated solid was filtered off