Rearrangement of N-benzyl-2-cyano-2-(hydroxyimino)acetamide

The reduction of N-benzyl-2-cyano-2-(hydroxyimino)acetamide resulted in the formation of N-benzyl-1,2-ethanediamine and N-benzyl-N'-methyl-1,2-ethanediamine in approximately an equimolar ratio. The formation of the two unexpected products is explained by the migration of a cyano group in a Beckmann-type rearrangement.