Reaction of some aromatic nitriles with hydroxylamine to give amides, and an alternative preparation of amidoximes

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Abstract
When certain aromatic nitriles containing electron-withdrawing substituents are treated with hydroxylamine in anhydrous methanol, substantial amounts of amides are formed, as well as the expected amidoximes. These amides probably result from initial attack by the oxygen atom of hydroxylamine or carbon and subsequent reaction of the intermediate (IV) with more hydroxylamine. The pure amidoximes can often be obtained in high overall yield by converting the nitriles into thioamides and treating these with hydroxylamine. p-Nitrobenzonitrile reacts slowly with methanol under neutral conditions, and with aqueous methanolic ammonia, to give methyl p-nitrobenzimidate.

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