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

HRID 1978395Notes

Reaction equation

HRID 1978395 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6](/[CH:10]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:7]=[CH:8][CH:9]=1)([O-])=O>O1CCCC1.[C].[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 5354248Ethyl 3-nitrocinnamate

Product 1

HCID 82314Ethyl 3-(3-Aminophenyl)propionateYield 61%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

(E)-Ethyl 3-(3-nitrophenyl)acrylate (12.1 g, 52.9 mmol) in tetrahydrofuran (100 ml) was hydrogenated over 10% palladium-Carbon (2.80 g) at atmospheric pressure. After removal of the catalyst, the filtrate was concentrated in vacuo. The residue was chromatographed on silica gel (100 g) with hexane-ethyl acetate (3:1) to give ethyl 3-(3-aminophenyl)propionate as a yellow oil (6.21 g, 61%).

Workup

  1. customAfter removal of the catalyst
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was chromatographed on silica gel (100 g) with hexane-ethyl acetate (3:1)

Sources & evidence

ORD record
ord-ccdd5f9aceb749079de69d25c9c3aad7
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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