Methyl 3-aminocinnamate → Methyl 3-(3-aminophenyl)propanoate

HRID 1270510Notes

Reaction equation

HRID 1270510 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH2:12])[CH:7]=1>C(O)C.[Pd]>[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH2:12])[CH:7]=1

Participants

4

Reactant 1

HCID 54385173Methyl 3-aminocinnamate

Product 1

HCID 10442275Methyl 3-(3-aminophenyl)propanoateYield 98.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-(3-amino-phenyl)-acrylic acid methyl ester (6 g) and 10% Pd on activated carbon (1 g) in ethanol (50 ml) was hydrogenated at 30 psi for 18 h and filtered over Celite. Removal of the volatiles in vacuo provided 3-(3-amino-phenyl)propionic acid methyl ester (6 g).

Workup

  1. filtrationfiltered over Celite
  2. customRemoval of the volatiles in vacuo

Sources & evidence

ORD record
ord-7555eef1c19c4a72872c7b55e294c982
Source dataset
uspto-grants-2007_04
Patent number
US07202257B2

Reaction notes

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