2-Methoxy-3,4-dinitrobenzoic Acid → 3,4-Diamino-2-methoxybenzoic acid

HRID 457763Notes

Reaction equation

HRID 457763 reaction equation
[CH3:1][O:2][C:3]1[C:11]([N+:12]([O-])=O)=[C:10]([N+:15]([O-])=O)[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6]>CO.[Pd]>[CH3:1][O:2][C:3]1[C:11]([NH2:12])=[C:10]([NH2:15])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6]

Participants

4

Reactant 1

HCID 185048962-Methoxy-3,4-dinitrobenzoic Acid

Product 1

HCID 185048683,4-Diamino-2-methoxybenzoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-methoxy-3,4-dinitrobenzoic acid (1.0 g) was dissolved in methanol (50 mL) and treated with 100 mg 10% palladium on carbon. The reaction mixture was purged with nitrogen and placed in an ice bath. Upon treatment with 5 mL formic acid, brisk effervescence was noticed which subsides upon further cooling. The reaction mixture was filtered through celite and concentrated to give a tan solid. (Decolorization occurs rapidly upon keeping) EIMS M+182, Exp. 182.

Workup

  1. customThe reaction mixture was purged with nitrogen
  2. customplaced in an ice bath
  3. filtrationThe reaction mixture was filtered through celite and
  4. concentrationconcentrated
  5. customto give a tan solid

Sources & evidence

ORD record
ord-e1d3b0caa5484bd583a0ab2e5886a796
Source dataset
uspto-grants-2007_03
Patent number
US07189739B2

Reaction notes

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