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

HRID 860021노트

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HRID 860021 반응식
[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

참가 물질

4

반응물 2

HCID 784Hydrogen PeroxideHCID 196975Quinoline, 6-fluoro-

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3e0888bca27b44688d986432b27adaf0
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07153849B2

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