Ethylenediamine → N-(2-aminoethyl)-N-(4-nitrophenyl)amine
Reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH2:11]([NH2:14])[CH2:12][NH2:13]>>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:13][CH2:12][CH2:11][NH2:14])=[CH:3][CH:4]=1)([O-:10])=[O:9]Participants
3
Procedure
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.
Sources & evidence
- ORD record
- ord-2b9ac13e5a59402b8a7e84fe2abb0787
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08993574B2
Reaction notes
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