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

HRID 2109999Notes

Reaction equation

HRID 2109999 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]>CO.[C].[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

4

Reactant 1

HCID 607264Methyl 2-amino-3-nitrobenzoate

Product 1

HCID 5718252,3-Diaminobenzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 178418390HCID 178418390, compoundSolvent

Procedure

After dissolving 2-amino-3-nitrobenzoic acid methyl ester (661 mg, 3.37 mmol) in methanol (30 ml), 10% palladium-carbon powder (5 mol %) was added under a nitrogen stream, and the mixture was stirred for 1 hour under a hydrogen atmosphere. The reaction mixture was filtered through celite, and the obtained filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=2/1) to obtain 2,3-diaminobenzoic acid methyl ester. The compound was identified by NMR.

Workup

  1. additionwas added under a nitrogen stream
  2. filtrationThe reaction mixture was filtered through celite
  3. concentrationthe obtained filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-cc5ff5ea01c5475ab33f729d48bb98be
Source dataset
uspto-grants-2009_04
Patent number
US07517875B2

Reaction notes

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