Selenium Dioxide → 6-Fluoro-7-methoxyquinoline-2-carbaldehyde

HRID 338910Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 338910
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]=[C:7]([CH3:14])[CH:6]=[CH:5]2.[Se](=O)=[O:16]>O1CCOCC1.O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]=[C:7]([CH:14]=[O:16])[CH:6]=[CH:5]2

Komponenten

4

Edukt 2

HCID 24007Selenium DioxideHCID 867074426-Fluoro-7-methoxy-2-methylquinoline

Produkt 1

HCID 867074436-Fluoro-7-methoxyquinoline-2-carbaldehydeAusbeute 73,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 218864351,4-Dioxane--water (1/1)Lösungsmittel

Versuchsvorschrift

To 6-fluoro-7-methoxy-2-methylquinoline (1.4 g, 7.3 mmol) in dioxane/water (10 ml/l mL) at ambient temperature was added selenium dioxide (0.97 g, 8.8 mmol) and the reaction was heated to reflux for 2-3 hours. After cooling, the reaction was filtered and the solids were washed with DCM. The filtrate was dried over MgSO4, filtered, and concentrated under reduced pressure. The crude material was purified by reverse phase chromatography (SP4, 25M, eluting with a gradient of water/ACN 100:0 to 0:100, 20 column volumes) to yield 6-fluoro-7-methoxyquinoline-2-carbaldehyde (1.1 g, 73% yield) as a tan solid.

Aufarbeitung

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 2-3 hours
  3. temperatureAfter cooling
  4. filtrationthe reaction was filtered
  5. washthe solids were washed with DCM
  6. dry with materialThe filtrate was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude material was purified by reverse phase chromatography (SP4, 25M
  10. washeluting with a gradient of water/ACN 100:0 to 0:100, 20 column volumes)

Quellen und Nachweise

ORD-Eintrag
ord-bea4fba9b6e94873b88fa45830637af6
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889704B2

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