Ethyl-m-nitrocinnamate → Ethyl 3-(3-Aminophenyl)propionate

HRID 16953Notes

Reaction equation

HRID 16953 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-])=O)[CH:8]=1)[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH2:13])[CH:8]=1)[CH3:2]

Participants

4

Reactant 1

HCID 94827Ethyl-m-nitrocinnamate

Product 1

HCID 82314Ethyl 3-(3-Aminophenyl)propionateYield 97.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-(3-nitro-phenyl)-acrylic acid ethyl ester (16.5 g, 74.6 mmol) and Pd/C (1.65 g) in methanol (200 mL) was stirred under 40 psi of H2 at RT for 2 h then filtered over celite. After removal the solvent, 14 g of 3-(3-amino-phenyl)-propionic acid ethyl ester was obtained and used directly without further purification. 1H-NMR (400 MHz, CDCl3): 7.11 (t, J=5.6 Hz, 1H), 6.67 (d, J=7.2 Hz, 1H), 6.63-6.61 (m, 2H), 4.13 (q, J=7.2 Hz, 2H), 2.87 (t, J=8.0 Hz, 2H), 2.59 (t, J=7.6 Hz, 2H), 1.34 (t, J=6.8 Hz, 3H).

Workup

  1. filtrationthen filtered over celite
  2. customAfter removal the solvent

Sources & evidence

ORD record
ord-99e6aac9d24c49f39af1e492dc3edb05
Source dataset
uspto-grants-2010_06
Patent number
US07737283B2

Reaction notes

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