Ethanol → Ethyl 2-(2,3,4-trifluoroanilino)propionate

HRID 985651Notes

Reaction equation

HRID 985651 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].[CH2:28](O)C>[Pd].C(OCC)(=O)C.CCCCCC>[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][CH2:19][CH3:28])=[O:17]

Participants

8

Reactant 5

HCID 702EthanolHCID 11748Methyl pyruvateHCID 24083Sulfuric acid magnesium salt (1:1)HCID 698711,2,3-Trifluoro-4-nitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 22015871Ethyl 2-(2,3,4-trifluoroanilino)propionate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21226206Ethyl acetate hexaneSolvent

Procedure

2,3,4-Trifluoronitrobenzene (3.54 g) and methyl pyruvate (2.32 g) were dissolved in ethanol (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 residue thus obtained was subjected to silica gel column chromatography (ethyl acetate-normal hexane=1:4) to give the title compound (4.84 g) as a pale yellow oily substance.

Workup

  1. filtrationAfter filtering off Pd-C and magnesium sulfate
  2. concentrationthe obtained filtrate was concentrated under reduced pressure
  3. customThe residue thus obtained

Sources & evidence

ORD record
ord-d7e1c4d700ed4f86894f9dd9c0b340b5
Source dataset
uspto-grants-2005_03
Patent number
US06872823B1

Reaction notes

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