Electrochemical amination of N,N-dimethylaniline

Yu.A. Lisitsyn

Kazan Federal University, Kazan, 420008 Russia

E-mail: ^*Yuri.Lisitsyn@kpfu.ru

Received January 17, 2021

ORIGINAL ARTICLE

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DOI: 10.26907/2542-064X.2021.1.20-28

For citation: Lisitsyn Yu.A. Electrochemical amination of N,N-dimethylaniline. Uchenye Zapiski Kazanskogo Universiteta. Seriya Estestvennye Nauki, 2021, vol. 163, no. 1, pp. 20–28. doi: 10.26907/2542-064X.2021.1.20-28. (In Russian)

Abstract

The process of indirect cathodic amination of N,N-dimethylaniline using the Ti(IV) – NH₂OH system was studied in aqueous solutions of 7–16 M sulfuric acid at 40 ?C. An increase in the acid concentration was accompanied by a raise in the efficiency of amine radical cation substitution. In 16 M H₂SO₄, N,N-dimethyl-p- and N,N-dimethyl-m-phenylenediamines (2:3) were obtained with the total current and dimethylaniline yields of 94% and 100%, respectively. Comparative analysis of the results of amination of N,N-dimethylaniline and aniline in the sulfuric acid media was carried out.

Keywords: cathode, Ti(IV)/Ti(III) mediator system, hydroxylamine, N,N-dimethylaniline, amine radical cation aromatic substitution

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