Ammonium Hydroxide → 6-Fluoro-7-methoxy-2-methylquinoline

HRID 338909Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 338909
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[O:9][CH3:10].[CH:11](=O)/[CH:12]=[CH:13]/[CH3:14].[OH-].[NH4+]>Cl>[F:1][C:2]1[CH:8]=[C:7]2[C:5](=[CH:4][C:3]=1[O:9][CH3:10])[N:6]=[C:13]([CH3:14])[CH:12]=[CH:11]2

Komponenten

5

Edukt 3

HCID 14923Ammonium HydroxideHCID 447466CrotonaldehydeHCID 27745334-Fluoro-3-methoxyaniline

Produkt 1

HCID 867074426-Fluoro-7-methoxy-2-methylquinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

To 4-fluoro-3-methoxyaniline (1.0 g, 7.1 mmol) in refluxing 6N HCl (20 mL) was added dropwise (E)-but-2-enal (0.99 g, 14 mmol) and the reaction was heated to reflux for 2 hours. After cooling, the reaction was neutralized with ammonium hydroxide and extracted with DCM. The combined organic phases were dried over MgSO4, filtered and concentrated under reduced pressure to yield 6-fluoro-7-methoxy-2-methylquinoline as a brown solid.

Aufarbeitung

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 2 hours
  3. temperatureAfter cooling
  4. extractionextracted with DCM
  5. dry with materialThe combined organic phases were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-eafa2ae0f97448f9b45b7affc89921aa
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889704B2

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