Ethyl 4-nitrocinnamate → Ethyl 3-(4-aminophenyl)propanoate

HRID 2101816Notes

Reaction equation

HRID 2101816 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][CH:5]=1)([O-])=O.[H][H]>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 1268038Ethyl 4-nitrocinnamateHCID 178418361HCID 178418361, compound

Product 1

HCID 10442595Ethyl 3-(4-aminophenyl)propanoateYield 69%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (E)-ethyl 3-(4-nitrophenyl)acrylate (commercially available from Aldrich, 5.00 g, 26.0 mmol) and 2.8 g of 10% Pd/C (wet, 50% water) in MeOH (26 mL) was shaken under 20 psi of hydrogen at room temperature for 20 hours. The mixture was then filtered through a pad of celite, the filtrate was concentrated, and the residue was purified through a short column of silica gel using 20% EtOAc/hexane as the eluent to give 3.48 g (69%) of the desired product ethyl 3-(4-aminophenyl)propanoate 47.2. MS ESI (pos.) m/e: 194 (M+H)+.

Workup

  1. filtrationThe mixture was then filtered through a pad of celite
  2. concentrationthe filtrate was concentrated
  3. customthe residue was purified through a short column of silica gel using 20% EtOAc/hexane as the eluent

Sources & evidence

ORD record
ord-2d96f88a88e346f6900d107e5043c922
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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