Studies on 4-hydroxyaminoquinoline 1-oxide and its related compounds. Synthesis of 3-chloro- and 3-bromo-4-aminoquinoline 1-oxide and presentation of chemical evidence for a new type of aromatic rearrangement of N,O-diarylhydroxylamines.

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The present paper deals with thermolyses of 4-hydroxyaminoquinoline 1-oxide (4HAQO) in acidic media and a new type of rearrangement of N, O-diarylhydroxylamine derived from 4HAQO and 4-hydroxyaminoquinoline. Thermolyses of 4-hydroxyaminoquinoline or-pyridine derivatives in hydrochloric or hydrobromic acid gave corresponding 3-halo-4-amino derivatives in relatively high yield. It was also found that N, O-di(4-quinolyl) hydroxylamine and N-(4-quinolyl)-O-(2, 4-dinitrophenyl) hydroxylamine were rearranged to a corresponding diaryl derivative, 3, 3'-(4-amino-4'-hydroxy) biquinoline and 3-(2'-hydroxy-3', 5'-dinitrophenyl)-4-aminoquinoline, respectively. Those facts presented the first chemical evidences for an aromatic rearrangement of N, O-diarylhydroxylamine which had already been predicted by Dewar.

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