Ethylenediamine → N-(2-aminoethyl)-N-(4-nitrophenyl)amine

Participants

Reaction Steps

From 1-chloro-4-nitrobenzene by heating in neat ethylene diamine to give N*1*-(4-nitro-phenyl)-ethane-1,2-diamine, followed by treatment with trifluoro-methanesulfonic acid 4,6-dimethyl-pyridin-2-yl ester (itself prepared according to J. Org. Chem., 63, 10048-51 (1998) using pyridine as base) in diglyme at reflux to afford N-(4,6-dimethyl-pyridin-2-yl)-N′-(4-nitro-phenyl)-ethane-1,2-diamine. Dimethylation with methyl iodide in THF in the presence of sodium hydride followed by catalytic hydrogenation over Raney nickel in methanol gives the required aniline.

Provenance & Evidence