Ethyl 3-(4-nitrophenyl)-2-propenoate → Ethyl 3-(4-aminophenyl)propanoate

HRID 1696469Notes

Reaction equation

HRID 1696469 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=1)[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([NH2:13])=[CH:11][CH:12]=1)[CH3:2]

Participants

4

Reactant 1

HCID 95370Ethyl 3-(4-nitrophenyl)-2-propenoate

Product 1

HCID 10442595Ethyl 3-(4-aminophenyl)propanoateYield 97.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-(4-nitrophenyl)acrylic acid ethyl ester (16.5 g, 74.6 mmol) and Pd/C (1.65 g) in MeOH (200 mL) was stirred under 40 psi of H2 at RT for 2 h. After filtration over Celite® and removal of the solvent, 14 g of 3-(4-aminophenyl)propionic acid ethyl ester was obtained. 1H NMR (400 MHz, CDCl3): δ 6.98 (d, J=8.0 Hz, 2H), 6.61 (d, J=8.4 Hz, 1H), 4.12 (q, J=7.2 Hz, 2H), 2.84 (t, J=8.0 Hz, 2H), 2.55 (t, J=7.6 Hz, 2H), 1.23 (t, J=7.2 Hz, 3H). MS (ESI): m/z: 194 (M+H+).

Workup

  1. filtrationAfter filtration
  2. customover Celite® and removal of the solvent

Sources & evidence

ORD record
ord-c31350ac895c4f609144c22a03f3abc7
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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