Chichibabin 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.

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.

Electrons from the N atom are then pushed towards the ring to regain aromaticity, forming a C=N bond and ejecting a hydride ion in the process.

[3] The mechanism above, loss of the hydride ion followed by abstraction of a proton, is supported by the fact that the nucleophile needs at least one hydrogen atom for the reaction to proceed.

Factors that influence the reaction rate include: Substrates with σ-dimethoxy groups don't aminate because they form a stable complex with sodium amide.