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

HRID 860021Notes

Reaction equation

HRID 860021 reaction equation
[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

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 196975Quinoline, 6-fluoro-

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
78 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3e0888bca27b44688d986432b27adaf0
Source dataset
uspto-grants-2006_12
Patent number
US07153849B2

Reaction notes

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