The Chichibabin reaction
is a method for producing 2-aminopyridine or 5-aminopyridine derivatives by the reaction of pyridine with sodium amide. It was reported by Aleksei Chichibabin
The direct amination of pyridine with sodium amide takes place in liquid ammonia
. Following the addition elimination mechanism first a nucleophilic NH2-
is added while a hydride (H-
) is leaving. The reaction takes place especially in 2 and 5 position of the Pyridine.
As electrophilic addition is only possible in 3 and 5 position of the pyridine ring the 2 and 5 positions became available for further synthesis by the Chichibabin reaction