Alkylation of quindoline and quindoline-11-carboxylic acid

The reaction between quindoline-11-carboxylic acid and alcohols in acid media gives the quindoline-11-carboxylate esters, but quindoline-11-carboxylic acid or its hydrochloride react with haloalkanes in the presence of basic catalysts and water binders to give 10-alkylquindoline-11-carboxylate esters. 10-Alkylquindolines were obtained similarly. Alkylation of 1-alkylquindoline-11-carboxylate esters in neutral media affords the quaternary salts.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1375–1379, October, 1986.