4-Chloro-3-nitrotoluene → 3-Nitro-4-(2-dimethylaminoethylamino)-toluene

HRID 373061Notes

Reaction equation

HRID 373061 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH3:12][N:13]([CH3:17])[CH2:14][CH2:15][NH2:16]>C(O)CC>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([NH:16][CH2:15][CH2:14][N:13]([CH3:17])[CH3:12])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

4

Reactant 2

HCID 69764-Chloro-3-nitrotolueneHCID 66053N,N-Dimethylethylenediamine

Product 1

HCID 198113893-Nitro-4-(2-dimethylaminoethylamino)-tolueneYield 11.2%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

A mixed solution of 4-chloro-3-nitrotoluene (1.30 g) and N,N-dimethylethylenediamine (1.34 g) in 1-propanol (20 ml) was refluxed for 24 hours and the solvent was distilled off under reduced pressure. The residue was dissolved in ethyl acetate and the solution was successively washed with water (×2) and saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure and the residue was purified by silica gel chromatography (eluent: chloroform:methanol=30:1) to give 0.19 g of N-(4-methyl-2-nitrophenyl)-N',N'-dimethylethylenediamine.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washthe solution was successively washed with water (×2) and saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was then distilled off under reduced pressure
  6. customthe residue was purified by silica gel chromatography (eluent: chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-7d3aed6a89e8489a8848d7c63c3c52a9
Source dataset
uspto-grants-1992_11
Patent number
US05162318

Reaction notes

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