Reaction of 3-(3-(2-nitrophenyl)-2-propenylidene)-2,4-pentanedione with hydroxylamine hydrochloride. formation of a 2-chloromethyleneindolin-3-one.

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Abstract

Reaction of 3-[3-(2-nitrophenyl)-2-propenylidene]-2, 4-pentanedione (3) with hydroxylamine hydrochloride in methanol gave a 1 : 1 mixture of (E)-4-[3-methoxy-3-(2-nitrophenyl)-1-propenyl]-3, 5-dimethylisoxazole (4) and (E)-4-[1-methoxy-3-(2-nitrophenyl)-2-propenyl]-3, 5-dimethylisoxazole (5) in 49.3% yield. Similarly, when acetonitrile was used as the solvent in this reaction, 2-(3, 5-dimethyl-4-isoxazolyl)-chloromethyleneindolin-3-one (6) (36.3%), (E)-4-acetyl-3-methyl-5-(2-nitrostyryl) isoxazole (7) (6.3%) and 4-[1-(hydroxyimino) ethyl]-3-methyl-7-(2-nitrophenyl)-1, 2-oxazepine (8) (1.8%) were obtained.

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