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

HRID 985660Notes

Reaction equation

HRID 985660 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-2502b5e9d068410b94b62b6a65c2985a
Source dataset
uspto-grants-2005_03
Patent number
US06872823B1

Reaction notes

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