4-Methoxy-2,3-dinitrotoluene → 3-Methoxy-6-methylbenzene-1,2-diamine

HRID 1879358Notes

Reaction equation

HRID 1879358 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[C:5]([N+:10]([O-])=O)[C:4]=1[N+:13]([O-])=O>CCO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[C:5]([NH2:10])[C:4]=1[NH2:13]

Participants

3

Reactant 1

HCID 122382934-Methoxy-2,3-dinitrotoluene

Product 1

HCID 139713463-Methoxy-6-methylbenzene-1,2-diamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Methoxy-6-methyl-benzene-1,2-diamine was synthesized by suspending 3.3 g of 1-methoxy-4-methyl-2,3-dinitro-benzene (Can. J. Chem. 65, 1233-1240, 1987) in 100 mL EtOH, evacuating 3 times with N2 and addition of 450 mg of 10wt % Pd/C. The reaction mixture was stirred under a H2 atmosphere (balloon) overnight. Filtration over a pad of celite and washing with 100 mL EtOH yielded after concentration in vacuo 2.2 g of the desired compound as brown oil.

Workup

  1. customevacuating 3 times
  2. additionwith N2 and addition of 450 mg of 10wt % Pd/C
  3. filtrationFiltration over a pad of celite
  4. washwashing with 100 mL EtOH
  5. customyielded
  6. concentrationafter concentration in vacuo 2.2 g of the desired compound as brown oil

Sources & evidence

ORD record
ord-5d2f3553f86746058ff97ae1b680d7a8
Source dataset
uspto-grants-2012_11
Patent number
US08314253B2

Reaction notes

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