Methyl 2-amino-3-nitrobenzoate → 2,3-Diaminobenzoic acid methyl ester

HRID 896382Notes

Reaction equation

HRID 896382 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-])=O)[C:5]=1[NH2:13]>C1COCC1.CO.[Pd]>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[C:5]=1[NH2:13]

Participants

5

Reactant 1

HCID 607264Methyl 2-amino-3-nitrobenzoate

Product 1

HCID 5718252,3-Diaminobenzoic acid methyl ester

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-amino-3-nitro-benzoic acid methyl ester (8.0 g, 40.8 mmol) with 10% Pd/C (800 mg) in THF (60 mL) and methanol (60 mL) was rocked under a hydrogen atmosphere (45 psi) for 45 min. Fitration and concentration afforded 2,3-diamino-benzoic acid methyl ester as a tan solid, that was used without further purification. 2-Acetoxymethyl-1H-benzoimidazole-4-carboxylic Acid Methyl Ester

Workup

  1. customfor 45 min
  2. concentrationFitration and concentration

Sources & evidence

ORD record
ord-1af4d59a0837408c91fe50449d01f4d5
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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