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Cyanomethylation of anthranilic acid

✍ Scribed by Miguel O. Mitchell; Ashley R. Hurley

Publisher: Journal of Heterocyclic Chemistry
Year: 2003
Tongue: English
Weight: 37 KB
Volume: 40
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570400323

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✦ Synopsis

Abstract

Anthranilic acid reacts with chloroacetonitrile and N,N‐diisopropylethylamine in DMF to yield 3‐imino‐2,3‐dihydro‐4,1‐benzoxazepin‐5(1__H__)‐one (1) as the only reaction product. Also known as Ashley's fluorescer, compound 1 is fluorescent and binds to calcium carbonate, including the calcium carbonate‐rich antennae of Daphnia pulex, the water flea.

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