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

HRID 458163

Reaction equation

HRID 458163 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-24cc46561fb94f3180bc0dfdf92c9821
Source dataset
uspto-grants-2007_03
Patent number
US07189847B2

Linked notes

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