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

HRID 1398732Notes

Reaction equation

HRID 1398732 reaction equation
[NH2:1][C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]>O1CCCC1.[Pd]>[NH2:1][C:2]1[C:11]([NH2:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 1

HCID 607264Methyl 2-amino-3-nitrobenzoate

Product 1

HCID 5718252,3-Diaminobenzoic acid methyl esterYield 99.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-amino-3-nitrobenzoate (29.6 g, 151 mmol) in tetrahydrofuran (containing stabilizer; 500 mL) was added palladium on carbon (3.0 g), and the mixture was purged with hydrogen and stirred under balloon pressure hydrogen at room temperature for 4 hr. The catalyst was removed by filtration, and the filtrate was concentrated in vacuo. The residual solid was washed with diethyl ether-n-hexane to give the title compound (25.0 g, 150 mmol, >99%) as a pale yellow solid.

Workup

  1. customthe mixture was purged with hydrogen
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated in vacuo
  4. washThe residual solid was washed with diethyl ether-n-hexane

Sources & evidence

ORD record
ord-08967595807d4cd3aae1a0a83bd82b29
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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