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

HRID 985649Notes

Reaction equation

HRID 985649 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]([O:18][CH3:19])(=[O:17])[C:14]([CH3:16])=O.S([O-])([O-])(=O)=O.[Mg+2].[H][H]>CO.[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]([O:18][CH3:19])=[O:17]

Participants

7

Reactant 4

HCID 11748Methyl pyruvateHCID 24083Sulfuric acid magnesium salt (1:1)HCID 698711,2,3-Trifluoro-4-nitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 22015876Methyl2-(2,3,4-trifluoroanilino)propionateYield 97.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2,3,4-Trifluoronitrobenzene (100 g) and methyl pyruvate (57.6 g) were dissolved in methanol (1000 ml). After adding 5% Pd-C (20.0 g) and anhydrous magnesium sulfate (90 g), the mixture was stirred at room temperature in a hydrogen atmosphere for 16 hours. Then the liquid reaction mixture was filtered through celite to thereby eliminate Pd-C and magnesium sulfate. The obtained filtrate was concentrated under reduced pressure and Florisil (100 g) and diethyl ether (700 ml) were added to the residue. After stirring for 2 hours, the liquid reaction mixture was filtered. The obtained organic layer was evaporated and the crystals thus precipitated were filtered while washing with hexane. Thus the title compound (128.2 g) was obtained as slightly yellowish crystals.

Workup

  1. customThen the liquid reaction mixture
  2. filtrationwas filtered through celite
  3. concentrationThe obtained filtrate was concentrated under reduced pressure and Florisil (100 g) and diethyl ether (700 ml)
  4. additionwere added to the residue
  5. customthe liquid reaction mixture
  6. filtrationwas filtered
  7. customThe obtained organic layer was evaporated
  8. customthe crystals thus precipitated
  9. filtrationwere filtered
  10. washwhile washing with hexane

Sources & evidence

ORD record
ord-a478350ee2d8406b8f54f71fdac1c5d3
Source dataset
uspto-grants-2005_03
Patent number
US06872823B1

Reaction notes

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