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

HRID 851869Notes

Reaction equation

HRID 851869 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[C:5]=1[NH2:14])([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:13]=[CH:12][CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[C:5]=1[NH2:14]

Participants

4

Reactant 1

HCID 607264Methyl 2-amino-3-nitrobenzoate

Product 1

HCID 5718252,3-Diaminobenzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 3-nitroanthranilate (1.44 g, 7.34 mmol) in methanol (50 mL) was added 10% Pd/C (300 mg), and the resulting mixture was stirred for 12 hours at room temperature under hydrogen atmosphere. The 10% Pd/C was removed, and the solvent was distilled off under reduced pressure, to give 1.22 (quantitative yield) of the desired compound in the form of a brown crystalline product.

Workup

  1. customThe 10% Pd/C was removed
  2. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-e047695225874545b352f0c7a7c8efa2
Source dataset
uspto-grants-2007_08
Patent number
US07253154B2

Reaction notes

Loading…