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

HRID 860021ノート

反応式

HRID 860021 の反応式
[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

参加物

4

反応物 2

HCID 784Hydrogen PeroxideHCID 196975Quinoline, 6-fluoro-

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3e0888bca27b44688d986432b27adaf0
出典データセット
uspto-grants-2006_12
特許番号
US07153849B2

反応ノート

読み込み中…