Cyclic imides. 16. Hydroxy and methoxy derivatives of aminophthalimide and phthalhydrazide

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.