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

HRID 338928Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 338928
[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].[NH4+].[OH-]>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-methylquinolineAusbeute 97,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

To 4-fluoro-3-methoxyaniline (4.0 g, 28 mmol) refluxing in 6N HCl (50 mL) was added dropwise (E)-but-2-enal (4.0 g, 57 mmol). The reaction was heated to reflux for 2 hours then cooled and neutralized with NH4OH. The organic phase was extracted with DCM. The combined organic phases dried over MgSO4, filtered and concentrated under reduced pressure to provide 6-fluoro-7-methoxy-2-methylquinoline (5.2 g, 96% yield) as a dark brown paste.

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 2 hours
  3. temperaturethen cooled
  4. extractionThe organic phase was extracted with DCM
  5. dry with materialThe combined organic phases dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-81cbd557125b4fc397eb629fe3092263
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889704B2

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