Reaction of some 1,4-benzoquinone mono-oximes with methanolic hydrogen chloride

When 2-methyl-1,4-benzoquinone 4-oxime (1) reacted with methanolic hydrogen chloride at 25–30 °C the product was 2-chloro-4,6-dimethoxy-3-methylaniline (2). Similarly 1,4-benzoquinone 4-oxime (7) gave 2-chloro-4,6-dimethoxyaniline (8), 3-methyl-1,4-benzoquinone 4-oxime (11) gave 2-chloro-4-methoxy-6 methoxymethylaniline (12) and 2-chloro-4-methoxy-6-methylaniline (13), and 2-methoxy-1,4-benzoquinone 4-oxime (19) gave 2-chloro-4,5-dimethoxyaniline (20).