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Cyanomethylation of anthranilic acid
Author(s) -
Mitchell Miguel O.,
Hurley Ashley R.
Publication year - 2003
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.5570400323
Subject(s) - chemistry , daphnia pulex , anthranilic acid , calcium carbonate , yield (engineering) , calcium , organic chemistry , medicinal chemistry , daphnia , ecology , materials science , crustacean , metallurgy , biology
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.