Pyruvic Acid → 2-(2,3,4-Trifluoroanilino)propionic acid

HRID 458172Notes

Reaction equation

HRID 458172 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]([OH:16])(=[O:15])[C:12]([CH3:14])=O.[H][H]>CC(O)C.[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]([OH:16])=[O:15]

Participants

6

Reactant 3

HCID 1060Pyruvic AcidHCID 774682,3,4-TrifluoroanilineHCID 178418361HCID 178418361, compound

Product 1

HCID 220158662-(2,3,4-Trifluoroanilino)propionic acidYield 91.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

2,3,4-Trifluoroaniline (4.18 g) and pyruvic acid (2.75 g) were dissolved in IPA (40 ml). After adding 10% Pd—C (0.21 g), the mixture was stirred at 40° C. under atmospheric pressure in a hydrogen atmosphere for 3 hours. After filtering off Pd—C, the obtained filtrate was concentrated under reduced pressure. Thus the title compound (5.69 g) was obtained as colorless crystals. Various spectral data of this product was identical with those of a specimen synthesized separately.

Workup

  1. filtrationAfter filtering off Pd—C
  2. concentrationthe obtained filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f6c69d2194fa4b979ee34d2aa5d3494b
Source dataset
uspto-grants-2007_03
Patent number
US07189847B2

Reaction notes

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