1,2-dimethoxy-5-methyl-3,4-dinitro-benzene → HCID 86641929, compound

HRID 220276Notes

Reaction equation

HRID 220276 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([N+:10]([O-])=O)=[C:5]([N+:13]([O-])=O)[C:4]=1[O:16][CH3:17]>CCO>[CH3:17][O:16][C:4]1[C:3]([O:2][CH3:1])=[CH:8][C:7]([CH3:9])=[C:6]([NH2:10])[C:5]=1[NH2:13]

Participants

3

Reactant 1

HCID 3481361,2-dimethoxy-5-methyl-3,4-dinitro-benzene

Product 1

HCID 86641929HCID 86641929, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3,4-Dimethoxy-6-methyl-benzene-1,2-diamine was synthesized by dissolving 11.5 g of 1,2-dimethoxy-5-methyl-3,4-dinitro-benzene in 300 mL EtOH, evacuating 3 times with N2 and adding 1.0 g of 10 wt % Pd/C. The reaction was stirred under a H2 atmosphere (balloon) for 2 days. Filtration over a pad of celite and washing with EtOH yielded after concentration in vacuo 8.8 g of 3,4-dimethoxy-6-methyl-benzene-1,2-diamine as brown oil.

Workup

  1. customevacuating 3 times with N2
  2. additionadding 1.0 g of 10 wt % Pd/C
  3. filtrationFiltration over a pad of celite
  4. washwashing with EtOH
  5. customyielded
  6. concentrationafter concentration in vacuo 8.8 g of 3,4-dimethoxy-6-methyl-benzene-1,2-diamine as brown oil

Sources & evidence

ORD record
ord-8c394fb3a8f14b9cb3b339f16ac139fd
Source dataset
uspto-grants-2012_06
Patent number
US08202885B2

Reaction notes

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