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

HRID 458169Notes

Reaction equation

HRID 458169 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-21d76d303956494a929e57147fafdd70
Source dataset
uspto-grants-2007_03
Patent number
US07189847B2

Reaction notes

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