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

HRID 458164Notes

Reaction equation

HRID 458164 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-d2ad7ddef95b4632983c80c5482b9973
Source dataset
uspto-grants-2007_03
Patent number
US07189847B2

Reaction notes

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