1,2-Dimethoxy-4,5-dinitrobenzene → 1,2-Diamino-4,5-dimethoxybenzene

HRID 852935Notes

Reaction equation

HRID 852935 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[C:6]([N+:12]([O-])=O)=[CH:5][C:4]=1[O:15][CH3:16]>CO>[CH3:16][O:15][C:4]1[CH:5]=[C:6]([NH2:12])[C:7]([NH2:9])=[CH:8][C:3]=1[O:2][CH3:1]

Participants

3

Reactant 1

HCID 2229891,2-Dimethoxy-4,5-dinitrobenzene

Product 1

HCID 1529391,2-Diamino-4,5-dimethoxybenzene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1,2-dimethoxy-4,5-dinitrobenzene (500 mg, 2.19 mmol) in MeOH (10 mL) was degassed and put under N2 atmosphere. A catalytic amount of Pd on charcoal (10%) was quenched with MeOH (1 mL) and transferred in one shot as a suspension in MeOH into the solution. Acetic acid (1.5 mL) was added and the black mixture was put under H2 atmosphere (1 atm), stirred at rt for 16 h. The mixture was filtered through a celite pad and rinsed with MeOH. The filtrate was concentrated in vacuo at 80° C. to afford the title compound 182 (residual acetic acid could not be removed from the product). 1H NMR: (DMSO-d6) δ (ppm): 6.23 (s, 2H), 3.56 (s, 6H). m/z: 169.3. (MH+).

Workup

  1. customA catalytic amount of Pd on charcoal (10%) was quenched with MeOH (1 mL)
  2. additionAcetic acid (1.5 mL) was added
  3. filtrationThe mixture was filtered through a celite pad
  4. washrinsed with MeOH
  5. concentrationThe filtrate was concentrated in vacuo at 80° C.

Sources & evidence

ORD record
ord-09aefbe344124e1f8eaa899f44aa2f03
Source dataset
uspto-grants-2007_08
Patent number
US07253204B2

Reaction notes

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