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

HRID 1978391Notes

Reaction equation

HRID 1978391 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>O1CCCC1.[C].[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

4

Reactant 1

HCID 1268038Ethyl 4-nitrocinnamate

Product 1

HCID 10442595Ethyl 3-(4-aminophenyl)propanoateYield 95%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

(E)-Ethyl 3-(4-nitrophenyl)acrylate (11.7 g, 52.9 mmol) in tetrahydrofuran (100 ml) was hydrogenated over 10% Palladium-Carbon (1.20 g) at atmospheric pressure. After removal of the catalyst, the filtrate was concentrated in vacuo to give ethyl 3-(4-aminophenyl)propionate as a yellow oil (9.66 g, 95%).

Workup

  1. customAfter removal of the catalyst
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-bef6075fa2cb49bc864e5e9b58ccb849
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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