M. Pieterse, H. J. Hertog
Sep 2, 2010
Citations
0
Influential Citations
12
Citations
Journal
Recueil des Travaux Chimiques des Pays-Bas
Abstract
The amination of 3-bromo-4-ethoxypyridine with potassium amide in liquid ammonia yielding 2-amino-4-ethoxypyridine as chief product has been reinvestigated. It is shown that 2-amino-5-bromo-4-ethoxypyridine is formed as a byproduct, probably via 3,5-dibromo-4-ethoxypyridine and 5-bromo-4-ethoxy-2,3-pyridyne as intermediates. In order to check the mechanism proposed for the process described above, aminations of 3- and 5-bromo-2,4-diethoxypyridine were studied. Both reactions yield 6-amino-2,4-diethoxypyridine as chief product. It was found that 3-bromo-2,4-diethoxypyridine was converted first into the 5-bromo-isomer. It seems likely that in both aminations 2,4-diethoxy-5,6-pyridyne is an intermediate.