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Chichibabin reaction

    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 in 1914.
    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