Chichibabin Amination

The preparation of 2‐aminopyridine from pyridine and sodium amide in boiling inert solvent (such as xylene, toluene, and benzene), is generally known as the Chichibabin amination. It has been reported that the yield of 2‐aminopyridine depends to a large extent on the condition of the sodium amide used in the synthesis. A second amino group might be introduced to the aromatic ring on increase the amount of sodium amide. The cyclic amine has been reported to form under these conditions when organic amine is connected to a pyridine ring. This reaction works not only for the pyridine series but also for other nitrogen‐containing heterocycles. This reaction has a general application in the preparation of nitrogen‐containing aromatic amines.