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The amination of 3-bromo-2-ethoxy-1,5-naphthyridine. A reinvestigation

✍ Scribed by H. J. W. van den Haak; H. C. van der Plas

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
424 KB
Volume
99
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

The reaction of 3‐bromo‐2‐ethoxy‐1,5‐naphthyridine with KNH~2~/NH~3~ was reinvestigated. The procedure, described in the literature for the preparation of the title compound does not lead to this compound but to the isomeric 3‐bromo‐1‐ethyl‐1,5‐naphthyridin‐2(1__H__)‐one. Reaction of this compound with KNH~2~/NH~3~ yields 3‐ and 4‐amino‐1‐ethyl‐1,5‐naphthyridin‐2(1__H__)‐one, the latter being the main product. The title compound was prepared on reacting 2,3‐dibromo‐1,5‐naphthyridine with sodium ethoxide. A mixture of 3‐ and 4‐amino‐2‐ethoxy‐1,5‐naphthyridine was obtained on amination of 3‐bromo‐2‐ethoxy‐1,5‐naphthyridine. In both cases the intermediacy of the respective 3,4‐didehydro compounds was proposed.

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