1-Bromo-2-nitrobenzene → N-(2-(dimethylamino)ethyl)-2-nitrobenzenamine

HRID 373066Notes

Reaction equation

HRID 373066 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH3:11][N:12]([CH3:16])[CH2:13][CH2:14][NH2:15]>C(O)CC>[N+:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:15][CH2:14][CH2:13][N:12]([CH3:16])[CH3:11])([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 113411-Bromo-2-nitrobenzeneHCID 66053N,N-Dimethylethylenediamine

Product 1

HCID 430957N-(2-(dimethylamino)ethyl)-2-nitrobenzenamineYield 91.7%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

To a solution of 2-bromonitrobenzene (10.23 g) in 1-propanol (100 ml) was added N,N-dimethylethylenediamine (13.41 g) and the mixture was refluxed for 3 days. The solvent was then distilled off under reduced pressure and the residue was purified by silica gel chromatography (eluent: chloroform:methanol=50:1) to give 9.72 g of N-(2-nitrophenyl)-N',N'-dimethylethylenediamine.

Workup

  1. temperaturethe mixture was refluxed for 3 days
  2. distillationThe solvent was then distilled off under reduced pressure
  3. customthe residue was purified by silica gel chromatography (eluent: chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-7e5fbfb6ecb4472d9ef6e025fd201440
Source dataset
uspto-grants-1992_11
Patent number
US05162318

Reaction notes

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