Electrophilic benzylation of 2‐aminopyridine ring

In the reaction of 2‐aminopyridine and its 3‐ or 5‐methyl derivatives with benzyl chloride used in a molar ratio of 1:2, benzylation of 2‐aminopyridine ring has been stated that 2‐amino‐3‐ or 5‐benzylpyridines c as the major products were obtained. Formation of c type compounds took place in the decomposition of 2‐benzylamino‐3‐ or 5‐benzylpyridines b obtained in the reaction of the 2‐benzylaminopyridines a , excess benzyl chloride was used. Production of the b and c compounds, where the benzyl substituent occupied position 3 or 5 in 2‐aminopyridine supported the electrophilic mechanism of the reaction (radical reaction was excluded). In the case of 2‐aminopyridine and its 3‐methyl derivative bis‐(2‐amino‐5‐pyridyl)phenylmethanes d were formed as the by‐products.