M. Pieterse, H. J. Hertog
Sep 2, 2010
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0
Influential Citations
23
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Journal
Recueil des Travaux Chimiques des Pays-Bas
Abstract
When reacted with potassium amide in liquid ammonia, both 3-chloro and 4-chloropyridine are converted into a mixture containing 3-amino and 4-aminopyridine in a ratio of 1:2. The same reaction product results from the animations of 3-iodo and 4-iodopyridine. The course of these reactions can be explained by a mechanism involving 3,4-pyridyne as an intermediate. 2-Chloro and 2-iodopyridine only yield 2-aminopyridine. Rearrangements via ethoxy derivatives of 3,4-pyridyne probably proceed in aminations of 3-bromo-6-ethoxypyridine and 4-bromo-5-ethoxypyridine. A shift of the substituent from position 3 to 2 occurs in the amination of 3-bromo-4-ethoxypyridine which yields 2-amino-4-ethoxypyridine. An abnormal rearrangement takes place during the amination of 2-bromo-6-ethoxypyridine, 4-amino-6-ethoxypyridine together with 2-amino-6-ethoxypyridine being formed.