Methyl 4-(methylamino)-3-nitrobenzoate → Methyl 3-amino-4-(methylamino)benzoate

HRID 2110013Notes

Reaction equation

HRID 2110013 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH3:11])=[C:6]([N+:12]([O-])=O)[CH:5]=1>C(OCC)(=O)C.CO.[C].[Pd]>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH3:11])=[C:6]([NH2:12])[CH:5]=1

Participants

4

Reactant 1

HCID 7650848Methyl 4-(methylamino)-3-nitrobenzoate

Product 1

HCID 15586064Methyl 3-amino-4-(methylamino)benzoate

Reagents, catalysts & solvents 2

HCID 21584119Ethylacetate methanolSolventHCID 178418390HCID 178418390, compoundSolvent

Procedure

After dissolving 4-methylamino-3-nitrobenzoic acid methyl ester (540 mg, 2.5 mmol) in ethyl acetate-methanol (2:1) (20 ml), 10% palladium-carbon powder (5 mol %) was added thereto under a nitrogen atmosphere. The mixture was stirred for 4 hours under a hydrogen atmosphere, and then the reaction mixture was filtered through celite. The filtrate was concentrated under reduced pressure to obtain 3-amino-4-methylaminobenzoic acid methyl ester. The compound was identified by LC-MS.

Workup

  1. additionwas added
  2. filtrationthe reaction mixture was filtered through celite
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6ec915b075b24c6e9b352c44ddabfa9f
Source dataset
uspto-grants-2009_04
Patent number
US07517875B2

Reaction notes

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