Regioselective Nitration of N-Alkyl Anilines using tert-Butyl Nitrite under Mild Condition

Priyanka Chaudhary; Surabhi Gupta; Nalluchamy Muniyappan; Shahulhameed Sabiah; Jeyakumar Kandasamy

doi:10.1021/acs.joc.8b02377

Regioselective Nitration of N-Alkyl Anilines using tert-Butyl Nitrite under Mild Condition

J Org Chem. 2019 Jan 4;84(1):104-119. doi: 10.1021/acs.joc.8b02377. Epub 2018 Dec 21.

Authors

Priyanka Chaudhary¹, Surabhi Gupta¹, Nalluchamy Muniyappan², Shahulhameed Sabiah², Jeyakumar Kandasamy¹

Affiliations

¹ Department of Chemistry , Indian Institute of Technology (BHU) , Varanasi , Uttar Pradesh 221005 , India.
² Department of Chemistry , Pondicherry University , Pondicherry 605014 , India.

PMID: 30540185
DOI: 10.1021/acs.joc.8b02377

Abstract

Regioselective ring nitration of N-alkyl anilines is reported using tert-butyl nitrite. The reactions proceed efficiently with a wide range of substrates providing synthetically useful N-nitroso N-alkyl nitroanilines in excellent yields which can be easily converted into N-alkyl phenylenediamines and N-alkyl nitroanilines using Zn-AcOH and HCl/MeOH, respectively.