5-(2-Dimethylamino-ethoxy)-2-nitro-phenylamine → 4-(2-(Dimethylamino)ethoxy)benzene-1,2-diamine

HRID 1909009Notes

Reaction equation

HRID 1909009 reaction equation
[CH3:1][N:2]([CH3:16])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([N+:13]([O-])=O)=[C:10]([NH2:12])[CH:11]=1>CCO>[CH3:1][N:2]([CH3:16])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[C:10]([NH2:12])[C:9]([NH2:13])=[CH:8][CH:7]=1

Participants

3

Reactant 1

HCID 203767455-(2-Dimethylamino-ethoxy)-2-nitro-phenylamine

Product 1

HCID 221677014-(2-(Dimethylamino)ethoxy)benzene-1,2-diamineYield 90.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-(2-Dimethylamino-ethoxy)-2-nitro-phenylamine (0.85 g, 3.77 mmol) was dissolved in EtOH and shaken under an atmosphere of H2 for 6 hours. The catalyst was removed by filtration. Evaporation in vacuo gave 4-(2-Dimethylamino-ethoxy)-benzene-1,2-diamine as a dark yellow oil (0.665 g, 90%). MS(ESI) m/z 196.0 (M+H)+

Workup

  1. customThe catalyst was removed by filtration
  2. customEvaporation in vacuo

Sources & evidence

ORD record
ord-dbe3ed15eff0481487933aa4d5ab9292
Source dataset
uspto-grants-2013_12
Patent number
US08598217B2

Reaction notes

Loading…