Hydrochloric Acid → 8-Fluoro-4-methylquinoline

HRID 131630Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 131630
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].Cl.[CH:10]([C:12]([CH3:14])=O)=[CH2:11]>C(O)C.O.O.O.O.O.O.[Fe](Cl)(Cl)Cl.[Cl-].[Zn+2].[Cl-]>[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:3]=1[N:4]=[CH:11][CH:10]=[C:12]2[CH3:14]

Komponenten

7

Edukt 3

HCID 313Hydrochloric AcidHCID 6570Methyl vinyl ketoneHCID 95842-Fluoroaniline

Produkt 1

HCID 167342108-Fluoro-4-methylquinoline

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3007855ZincchlorideKatalysatorHCID 16211236Trichloroiron;hexahydrateKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 2-fluoroaniline (25 ml) in ethanol (185 ml) was added concentrated hydrochloric acid (21 ml), iron (III) chloride hexahydrate (111 g) and zinc (II) chloride (4.1 g) and the resulting mixture was heated to 60° C. Methyl vinyl ketone (25 ml) was added dropwise over 45 min. then the mixture was refluxed for 2 hrs. The reaction mixture was allowed to cool then evaporated under reduced pressure. The resulting oil was basified to pH 12 with 2M sodium hydroxide solution, filtered through arbocel and then the aqueous was extracted with ethyl acetate (×2). The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography over silica, eluting with i-hexane/diethyl ether (3:1) followed by i-hexane/diethyl ether (2:1) to give the sub-title compound as a solid (8.25 g).

Aufarbeitung

  1. temperaturethe mixture was refluxed for 2 hrs
  2. temperatureto cool
  3. customthen evaporated under reduced pressure
  4. filtrationfiltered through arbocel
  5. extractionthe aqueous was extracted with ethyl acetate (×2)
  6. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe residue was purified by column chromatography over silica
  10. washeluting with i-hexane/diethyl ether (3:1)

Quellen und Nachweise

ORD-Eintrag
ord-34942b22469847ef93fc4322a781827e
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384951B2

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