H. V. D. Haak, H. Plas
Sep 2, 2010
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Journal
Recueil des Travaux Chimiques des Pays-Bas
Abstract
The reaction of 3-bromo-2-ethoxy-1,5-naphthyridine with KNH2/NH3 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(1H)-one. Reaction of this compound with KNH2/NH3 yields 3- and 4-amino-1-ethyl-1,5-naphthyridin-2(1H)-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.