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

HRID 2409426Notes

Reaction equation

HRID 2409426 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>CO.O1CCCC1.[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 95370Ethyl 3-(4-nitrophenyl)-2-propenoate

Product 1

HCID 10442595Ethyl 3-(4-aminophenyl)propanoateYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Ethyl 3-(4-nitrophenyl)acrylate (3 g, 13.56 mmol) was dissolved in methanol/tetrahydrofuran (20 ml), added with 10%-palladium (Pd) (300 mg). The resulting mixture was stirred for one day under hydrogen gas at room temperature and filtered using celite to remove 10%-palladium (Pd). The filtrate was then concentrated under reduced pressure. The residue was then purified by flash column chromatography (hexane:ethylacetate=3:1) to obtain the title compound (2.14 g, yield: 82%, colorless liquid).

Workup

  1. filtrationfiltered
  2. customto remove 10%-palladium (Pd)
  3. concentrationThe filtrate was then concentrated under reduced pressure
  4. customThe residue was then purified by flash column chromatography (hexane:ethylacetate=3:1)

Sources & evidence

ORD record
ord-caae9581f96c403d86955491042c3e58
Source dataset
uspto-grants-2014_08
Patent number
US08815891B2

Reaction notes

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