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Synthesis and bromination of 4-alkylamino-N-alkyl-1,8-naphthalimides

Authors
Journal
Dyes and Pigments
0143-7208
Publisher
Elsevier
Publication Date
Volume
43
Issue
2
Identifiers
DOI: 10.1016/s0143-7208(99)00045-5
Keywords
  • Naphthalimides
  • Bromination
  • Fluorescent
  • Gabriel Synthesis
  • Dealkylation

Abstract

Abstract 4-Alkylamino- N-alkyl-1,8-naphthalimides were prepared from 4-chloro-1,8-naphthalic anhydride and from 4-amino-1,8-naphthalimide. It was found that the amino nitrogen of 4-amino- N-alkyl-1,8-naphthalimides is nucleophilic enough to participate in nucleophilic displacement reactions without the need for added base, despite being a vinylogous amide. Bromination of 4-alkylamino- N-alkyl-1,8-naphthalimides using molecular bromine was found to occur in the absence of a Lewis acid catalyst, and to be regiospecific, yielding only the 3-bromo isomer. Extended reaction times and the use of excess bromine result in dealkylation of the 4-alkylamino substituent, but no polybromination of the naphthalimide ring system.

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