Methyl 4-[(tert-butoxy)carbonylamino]-3-nitrobenzoate → Methyl 3-amino-4-[(tert-butoxycarbonyl)amino]benzoate

HRID 2110014Notes

Reaction equation

HRID 2110014 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[C:6]([N+:18]([O-])=O)[CH:5]=1>C(OCC)(=O)C.CO.[C].[Pd]>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])=[C:6]([NH2:18])[CH:5]=1

Participants

4

Reactant 1

HCID 22988663Methyl 4-[(tert-butoxy)carbonylamino]-3-nitrobenzoate

Product 1

HCID 18621647Methyl 3-amino-4-[(tert-butoxycarbonyl)amino]benzoate

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

4-tert-Butoxycarbonylamino-3-nitrobenzoic acid methyl ester (1.11 g, 3.75 mmol) was dissolved in ethyl acetate-methanol (1:1) (30 ml). Next, 10% palladium-carbon powder (200 mg, 5 mol %) was added to the aqueous solution under a nitrogen atmosphere, and the mixture was stirred overnight under a hydrogen atmosphere. The reaction mixture was filtered with celite, and the filtrate was concentrated under reduced pressure to obtain 3-amino-4-tert-butoxycarbonylaminobenzoic acid methyl ester. The compound was identified by LC-MS.

Workup

  1. filtrationThe reaction mixture was filtered with celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f3c73245fabd480e879f1a3c3e52ab34
Source dataset
uspto-grants-2009_04
Patent number
US07517875B2

Reaction notes

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