Methyl pyruvate → Methyl2-(2,3,4-trifluoroanilino)propionate

HRID 458162Notes

Reaction equation

HRID 458162 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]([O:16][CH3:17])(=[O:15])[C:12]([CH3:14])=O.S([O-])([O-])(=O)=O.[Mg+2].[H][H]>CO.[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]([O:16][CH3:17])=[O:15]

Participants

7

Reactant 4

HCID 11748Methyl pyruvateHCID 24083Sulfuric acid magnesium salt (1:1)HCID 774682,3,4-TrifluoroanilineHCID 178418361HCID 178418361, compound

Product 1

HCID 22015876Methyl2-(2,3,4-trifluoroanilino)propionateYield 95.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2,3,4-Trifluoroaniline (2.94 g) and methyl pyruvate (2.04 g) were dissolved in methanol (30 ml). After adding 5% Pd—C (2.0 g) and anhydrous magnesium sulfate (2.65 g), the mixture was stirred at 50° C. in a hydrogen atmosphere for 16 hours. After filtering off Pd—C and magnesium sulfate, the obtained filtrate was concentrated under reduced pressure. The crystals thus precipitated were filtered while washing with hexane. Thus the title compound (4.44 g) was obtained as slightly yellowish crystals. Various spectral data of this product was identical with those obtained in Example 5.

Workup

  1. filtrationAfter filtering off Pd—C and magnesium sulfate
  2. concentrationthe obtained filtrate was concentrated under reduced pressure
  3. customThe crystals thus precipitated
  4. filtrationwere filtered
  5. washwhile washing with hexane

Sources & evidence

ORD record
ord-f47d0f32f0ae4384a71b6cddcdd5d4c1
Source dataset
uspto-grants-2007_03
Patent number
US07189847B2

Reaction notes

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