Unusual nucleophilic substitution in the nitrophthalimide series

Article abstract of DOI:10.1007/BF02503501

The reactions of 3-and 4-nitrophthalimides with hydroxylamine in aqueous alcohol media were studied. A mixture of 3-amino-4-nitro-and 4-amino-5-nitrophthalimides is formed in the case of 4-nitrosubstituted derivative, whereas 3,6-dihydroxyphthalimide is unexpectedly found to be the main product of the reaction of 4-nitrosubstituted derivative. A possible mechanism of the transformation was suggested.