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

HRID 8431
Notes
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Reaction equation

HRID 8431 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 23938
Palladium
Catalyst
HCID 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-3aa39437285a4e61ad16bed02546d92a
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07087778B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes