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

HRID 458170Notes

Reaction equation

HRID 458170 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>CC(O)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

5

Reactant 2

HCID 1060Pyruvic AcidHCID 698711,2,3-Trifluoro-4-nitrobenzene

Product 1

HCID 220158662-(2,3,4-Trifluoroanilino)propionic acidYield 97.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
40 °C

Procedure

2,3,4-Trifluoronitrobenzene (5.03 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 a hydrogen gas pressure of 2.94 MPa for 3 hours. After filtering off Pd—C, the obtained filtrate was concentrated under reduced pressure. Thus the title compound (6.09 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-3d970164d1ec4f8584ed4836261d5449
Source dataset
uspto-grants-2007_03
Patent number
US07189847B2

Reaction notes

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