1-(2-Methoxy-ethoxy)-2,3-dinitro-benzene → 3-(2-Methoxyethoxy)benzene-1,2-diamine

HRID 18597Notes

Reaction equation

HRID 18597 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-])=O)[C:7]=1[N+:15]([O-])=O>CO>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH2:12])[C:7]=1[NH2:15]

Participants

3

Reactant 1

HCID 865958811-(2-Methoxy-ethoxy)-2,3-dinitro-benzene

Product 1

HCID 684142223-(2-Methoxyethoxy)benzene-1,2-diamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.80 g (7.43 mmol) 1-(2-Methoxy-ethoxy)-2,3-dinitro-benzene were dissolved in 250 mL MeOH. The solution was evacuated and rinsed with argon several times. 250 mg palladium on charcoal (10%) were added and again the mixture was evacuated and rinsed with argon several times. Finally argon was exchanged by hydrogen (balloon filled with hydrogen) and the mixture was stirred for 2 h at room temperature. The reaction mixture was filtered over “Celite” and the filter residue was washed with 100 mL MeOH. The filtrate was concentrated under vacuo to give pure 3-(2-Methoxy-ethoxy)-benzene-1,2-diamine as a brown oil. Yield: 1.33 g MS (ES+): m/e=183.

Workup

  1. customThe solution was evacuated
  2. washrinsed with argon several times
  3. addition250 mg palladium on charcoal (10%) were added
  4. customagain the mixture was evacuated
  5. washrinsed with argon several times
  6. filtrationThe reaction mixture was filtered over “Celite”
  7. washthe filter residue was washed with 100 mL MeOH
  8. concentrationThe filtrate was concentrated under vacuo

Sources & evidence

ORD record
ord-1e7ce3ef2d6a46f09fcf1321274694d2
Source dataset
uspto-grants-2010_06
Patent number
US07741341B2

Reaction notes

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