Science of Synthesis

Spitzner, D., Science of Synthesis Knowledge Updates, (2016) 1, 189.

The preparation of pyridin-2-amine from pyridine and sodium amide in a boiling inert solvent (such as xylene, toluene, or benzene) is generally known as the Chichibabin amination. It has been reported that the yield of pyridin-2-amine 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 upon increasing the amount of sodium amide. A cyclic amine may form under these conditions when an amine is tethered to a pyridine ring. This reaction works not only for the pyridine series but also for other nitrogen-containing heterocycles, and is generally applicable in the preparation of nitrogen-containing aromatic amines.[‌559‌]

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