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

HRID 8432

Reaktionsgleichung

Reaktionsgleichung von HRID 8432
[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]

Komponenten

8

Edukt 5

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-ef41386ffd2e4542a863081859790979
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087778B2

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