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Cyclic imides. 16 . Hydroxy and methoxy derivatives of aminophthalimide and phthalhydrazide
Author(s) -
Caswell Lyman R.,
Cavasos Gayle
Publication year - 1995
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570320339
Subject(s) - chemistry , phthalimides , imide , alkoxy group , potassium , toluene , medicinal chemistry , fermi resonance , fluorescence , alkylation , alkyl , infrared spectroscopy , organic chemistry , catalysis , physics , phthalimide , quantum mechanics
Treatment of N ‐alkyl derivatives of 3,6‐dichlorophthalimide and 4,5‐dichlorophthalimide with potassium nitrite gave 3‐hydroxy‐6‐nitro‐ and 4‐hydroxy‐5‐nitrophthalimides. The potassium salts of these phenols were alkylated by dialkyl sulfates. The products were reduced to the 3‐amino‐6‐alkoxy‐ and 4‐amino‐5‐alkoxyphthalimides, and the fluorescence emission spectra of these products were measured. Hydrazinolysis of the phthalimides in a toluene medium gave phthalhydrazides. The luminescence spectra of several aminophthalhydrazides were measured. The infrared and proton magnetic resonance spectra of these and of some nitrophthalhydrazides were measured and aspects of these spectra characteristic of phthalhydrazides were identified.