N-Anions of heteroaromatic amines

The alkylation of the N-anions of 2- and 4-aminopyridines, 1-aminoisoquinoline, and 2-amino-1-ethylbenzimidazole with C₂-C₄ alkyl halides in liquid ammonia leads to the formation of a mixture of the products of mono- and dialkylation at the NH₂ group (usually with a predominance of the latter). The role of stepwise processes and the yield of the dialkyl derivative increase on passing from alkyl bromides to iodides and from the heavier and branched radicals (C₄H₉, i-C₃H₇) to lighter radicals (C₂H₅).For communication V, see [1].Deceased.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 967–971, July, 1973.