Ethyl pyruvate → Ethyl 2-(2,3,4-trifluoroanilino)propionate

HRID 985652Notes

Reaction equation

HRID 985652 reaction equation
[F:1][C:2]1[C:8]([F:9])=[C:7]([F:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[C:11]([O:16][CH2:17][CH3:18])(=[O:15])[C:12]([CH3:14])=O.S([O-])([O-])(=O)=O.[Mg+2].[H][H]>CO.[Pd]>[F:1][C:2]1[C:8]([F:9])=[C:7]([F:10])[CH:6]=[CH:5][C:3]=1[NH:4][CH:12]([CH3:14])[C:11]([O:16][CH2:17][CH3:18])=[O:15]

Participants

7

Reactant 4

HCID 12041Ethyl pyruvateHCID 24083Sulfuric acid magnesium salt (1:1)HCID 774682,3,4-TrifluoroanilineHCID 178418361HCID 178418361, compound

Product 1

HCID 22015871Ethyl 2-(2,3,4-trifluoroanilino)propionateYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2,3,4-Trifluoroaniline (2.94 g) and ethyl pyruvate (2.32 g) were dissolved in methanol (30 ml). After adding 5% Pd-C (2.0 g) and anhydrous magnesium sulfate (2.65 g), the mixture was stirred at 50° C. in a hydrogen atmosphere for 16 hours. After filtering off Pd-C and magnesium sulfate, the obtained filtrate was concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate-normal hexane=1:4) to thereby give the title compound (4.69 g) as a pale yellow oily substance. Various spectral data of this product was identical with those obtained in Example 7.

Workup

  1. filtrationAfter filtering off Pd-C and magnesium sulfate
  2. concentrationthe obtained filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4e59a014b2354e0e9573a2edbdf6d024
Source dataset
uspto-grants-2005_03
Patent number
US06872823B1

Reaction notes

Loading…