Hydrogen Peroxide → 6-Fluoro-1-oxo-1lambda~5~-quinoline

HRID 860021Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 860021
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[OH:12]O>C(O)(=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N+:8]([O-:12])=[CH:7][CH:6]=[CH:5]2

Komponenten

4

Edukt 2

HCID 784Hydrogen PeroxideHCID 196975Quinoline, 6-fluoro-

Produkt 1

HCID 198986466-Fluoro-1-oxo-1lambda~5~-quinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
78 °C

Versuchsvorschrift

The 6-fluoroquinoline from Step A (6.0 g, 40.8 mmol) in glacial acetic acid (60 mL) is treated dropwise with hydrogen peroxide (14 mL) and heated with an oil bath to 78° C. overnight. The reaction mixture is concentrated at reduced pressure and the concentrate basified with solid sodium carbonate and extracted with dichloromethane. The extracts are dried over anhydrous magnesium sulfate, filtered, and concentrated to a light yellow solid (6.0 g). The residue is flash chromatographed on silica gel Merck-60 using a gradient of methanol (5–10%) in dichloromethane to provide the title compound as a white solid (0.99 g), m.p. 105–106° C.

Aufarbeitung

  1. concentrationThe reaction mixture is concentrated at reduced pressure
  2. extractionextracted with dichloromethane
  3. dry with materialThe extracts are dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to a light yellow solid (6.0 g)
  6. customchromatographed on silica gel Merck-60

Quellen und Nachweise

ORD-Eintrag
ord-3e0888bca27b44688d986432b27adaf0
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07153849B2

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