Addition of primary aliphatic amines to 1,2-benzoquinone. The absence of reaction between a secondary amide and 1,2-benzoquinone

The addition of methylamine or ethylamine to 1,2-benzoquinone results in two isomeric major products, a 4,5-diamino-1,2-benzoquinone monoimine and a 2,5-diamino-1,4-benzoquinone monoimine. Addition of n-propylamine or n-butylamine to 1,2-benzoquinone affords the 2,5-diamino-1,4-benzoquinone monoimine. No reaction was detected between N-methylacetamide and 1,2-benzoquinone.