1,4-Dimethoxy-2,3-dinitrobenzene → 3,6-Dimethoxybenzene-1,2-diamine

HRID 220274Notes

Reaction equation

HRID 220274 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[C:5]([N+:11]([O-])=O)[C:4]=1[N+:14]([O-])=O>CCO>[CH3:10][O:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([NH2:14])[C:5]=1[NH2:11]

Participants

3

Reactant 1

HCID 2432231,4-Dimethoxy-2,3-dinitrobenzene

Product 1

HCID 116296603,6-Dimethoxybenzene-1,2-diamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3,6-Dimethoxy-benzene-1,2-diamine was synthesized by dissolving 6.0 g of 1,4-dimethoxy-2,3-dinitro-benzene (Eur. J. Org. Chem. 2006, 2786-2794) in 220 mL EtOH, evacuating 3 times with N2 and adding 600 mg of 10 wt % Pd/C. The reaction was stirred under a H2 atmosphere (balloon). Another 300 mg of 10 wt % Pd/C were added after 2 days and the mixture was stirred for another 24 h. Filtration over a pad of celite and washing with EtOH and EtOAc yielded after concentration in vacuo 4.3 g of 3,6-dimethoxy-benzene-1,2-diamine as black solid.

Workup

  1. customevacuating 3 times with N2
  2. additionadding 600 mg of 10 wt % Pd/C
  3. additionAnother 300 mg of 10 wt % Pd/C were added after 2 days
  4. stirringthe mixture was stirred for another 24 h
  5. filtrationFiltration over a pad of celite
  6. washwashing with EtOH and EtOAc
  7. customyielded
  8. concentrationafter concentration in vacuo 4.3 g of 3,6-dimethoxy-benzene-1,2-diamine as black solid

Sources & evidence

ORD record
ord-736e615ab2df479dacbbe30c64833a26
Source dataset
uspto-grants-2012_06
Patent number
US08202885B2

Reaction notes

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