3-(3-Dimethylcarbamoyl-4-nitrophenyl)propionic acid ethyl ester → 3-(4-Amino-3-dimethylcarbamoylphenyl)propionic acid ethyl ester

HRID 423270Notes

Reaction equation

HRID 423270 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[C:9]([C:16](=[O:20])[N:17]([CH3:19])[CH3:18])[CH:8]=1)[CH3:2]>O1CCCC1.C(O)C.[H][H].[C].[Pd]>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[C:9]([C:16](=[O:20])[N:17]([CH3:18])[CH3:19])[CH:8]=1)[CH3:2]

Participants

6

Reactant 1

HCID 666758683-(3-Dimethylcarbamoyl-4-nitrophenyl)propionic acid ethyl ester

Product 1

HCID 666764553-(4-Amino-3-dimethylcarbamoylphenyl)propionic acid ethyl esterYield 69.6%

Reagents, catalysts & solvents 4

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

3-(3-Dimethylcarbamoyl-4-nitrophenyl)propionic acid ethyl ester (1.52 g) was dissolved in a mixed solution of THF (tetrahydrofuran) (15 mL) and ethanol (15 mL). 7.5% (w/w) palladium-carbon (300 mg) was added thereto, followed by stirring overnight at normal pressure in hydrogen atmosphere. The reaction solution was filtered through a Celite pad and concentrated to give the title compound (0.950 g) as a pale yellow oil.

Workup

  1. filtrationThe reaction solution was filtered through a Celite pad
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-56c0dc3ec3d6403f8f9005fc79de0d61
Source dataset
uspto-grants-2012_01
Patent number
US08101774B2

Reaction notes

Loading…