ethyl(2E)-3-(4-amino-2-fluorophenyl)acrylate → Ethyl 3-(4-amino-2-fluorophenyl)propanoate

HRID 507917Notes

Reaction equation

HRID 507917 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:4]([F:15])[CH:3]=1>C(O)C.[C].[Pd]>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:4]([F:15])[CH:3]=1

Participants

4

Reactant 1

HCID 20536506ethyl(2E)-3-(4-amino-2-fluorophenyl)acrylate

Product 1

HCID 23157234Ethyl 3-(4-amino-2-fluorophenyl)propanoateYield 79%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

Ethyl(2E)-3-(4-amino-2-fluorophenyl)acrylate (12.4 g, 59.3 mmol) was dissolved in ethanol (120 mL), and 10% palladium-carbon (50% water-containing product, 4.0 g) was added. The mixture was stirred under a hydrogen atmosphere (balloon pressure) at room temperature for 12 hr. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (20%-50% ethyl acetate/hexane) to give the title compound (9.89 g, yield 79%) as a pale-brown oil.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (20%-50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8b8ce9fd78054428b61eac448309b81d
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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