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

HRID 1012059Notes

Reaction equation

HRID 1012059 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]>CCO.[Pd]>[NH2:13][C:5]1[C:6]([NH2:10])=[CH:7][CH:8]=[CH:9][C:4]=1[C:3]([O:2][CH3:1])=[O:14]

Participants

4

Reactant 1

HCID 607264Methyl 2-amino-3-nitrobenzoate

Product 1

HCID 5718252,3-Diaminobenzoic acid methyl esterYield 93.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of methyl-2-amino-3-nitrobenzoate (530 mg) and 10% Pd/C (55 mg) in EtOH (10 ml) was stirred under an atmosphere of hydrogen at ambient temperature for 16 h. The catalyst was removed by filtration through Celite and the filtrate reduced in vacuo to give methyl 2,3-diaminobenzoate (420 mg) as a yellow/brown oil which solidified on standing.

Workup

  1. customThe catalyst was removed by filtration through Celite

Sources & evidence

ORD record
ord-3eb3a4dffdde4ef1b809145830eb4faa
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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