3-(2-Methyl-4-nitro-phenyl)-acrylic Acid Methyl Ester → Methyl 3-(4-amino-2-methylphenyl)propanoate

HRID 860649Notes

Reaction equation

HRID 860649 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][C:7]=1[CH3:15].[H][H]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:16])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][C:7]=1[CH3:15]

Participants

5

Reactant 2

HCID 688396503-(2-Methyl-4-nitro-phenyl)-acrylic Acid Methyl EsterHCID 178418361HCID 178418361, compound

Product 1

HCID 54187007Methyl 3-(4-amino-2-methylphenyl)propanoateYield 77.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-(2-Methyl-4-nitro-phenyl)-acrylic acid methyl ester (1.47 g, 6.64 mmol) and 5% Pd/C (0.29 g) in MeOH (100 mL) is exposed to a hydrogen atmosphere (60 psi) for 12 h. The mixture is filtered through Celite and purified by flash chromatography to yield the title compound (0.99 g, 77%).

Workup

  1. filtrationThe mixture is filtered through Celite
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-83720905f0f5408f91f7025b1c53d626
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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