Chichibabin reaction

Chichibabin reaction
Named after	Aleksei Chichibabin
Reaction type	Substitution reaction
Identifiers
RSC ontology ID	RXNO:0000527

The Chichibabin reaction (pronounced ' (chē')-chē-bā-bēn) is a method for producing 2-aminopyridine derivatives by the reaction of pyridine with sodium amide. It was reported by Aleksei Chichibabin in 1914.^[1] The following is the overall form of the general reaction:

The direct amination of pyridine with sodium amide can take place in liquid ammonia or an aprotic solvent such as xylene is commonly used. Following the addition elimination mechanism first a nucleophilic NH₂⁻ is added while a hydride (H⁻) is leaving. The reaction formally is a nucleophilic substitution of hydrogen S_NH.

Ciganek describes an example of an intramolecular Chichibabin reaction in which a nitrile group on a fused ring is the source of nitrogen in amination.^[2]

^ Chichibabin, A. E.; Zeide, O. A. (1914). "New Reaction for Compounds Containing the Pyridine Nucleus". Zhur. Russ. Fiz. Khim. Obshch (J. Russ. Phys. Chem. Soc.). 46: 1216–36.
^ Ciganek, E. (1992). "Tertiary Carbinamines by Addition of Organocerium Reagents to Nitriles and Ketimines". Journal of Organic Chemistry. 57 (16): 4521–7. doi:10.1021/jo00042a037.

[1] Chichibabin, A. E.; Zeide, O. A. (1914). "New Reaction for Compounds Containing the Pyridine Nucleus". Zhur. Russ. Fiz. Khim. Obshch (J. Russ. Phys. Chem. Soc.). 46: 1216–36.

[2] Ciganek, E. (1992). "Tertiary Carbinamines by Addition of Organocerium Reagents to Nitriles and Ketimines". Journal of Organic Chemistry. 57 (16): 4521–7. doi:10.1021/jo00042a037.

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