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

HRID 985657Notes

Reaction equation

HRID 985657 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[N+:10]([O-])=O.[C:13]([OH:18])(=[O:17])[C:14]([CH3:16])=O.[H][H]>C(O)(C)C.[Pd]>[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[NH:10][CH:14]([CH3:16])[C:13]([OH:18])=[O:17]

Participants

6

Reactant 3

HCID 1060Pyruvic AcidHCID 698711,2,3-Trifluoro-4-nitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 220158662-(2,3,4-Trifluoroanilino)propionic acidYield 98.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

2,3,4-Trifluoronitrobenzene (5.03 g) and pyruvic acid (2.75 g) were dissolved in isopropanol (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 (6.11 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-d6f45f93310c4a10b7268a69b206eac5
Source dataset
uspto-grants-2005_03
Patent number
US06872823B1

Reaction notes

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