Hydrochloric Acid → 6-Fluoro-8-methoxy-2-methylquinoline

HRID 338915Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 338915
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([O:9][CH3:10])[CH:3]=1.Cl.[CH:12](=O)/[CH:13]=[CH:14]/[CH3:15].[NH4+].[OH-]>>[F:1][C:2]1[CH:8]=[C:7]2[C:5](=[C:4]([O:9][CH3:10])[CH:3]=1)[N:6]=[C:14]([CH3:15])[CH:13]=[CH:12]2

Komponenten

5

Edukt 4

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 447466CrotonaldehydeHCID 135322284-Fluoro-2-methoxyaniline

Produkt 1

HCID 867074466-Fluoro-8-methoxy-2-methylquinolineAusbeute 99,8 %

Versuchsvorschrift

To 4-fluoro-2-methoxyaniline (370 mg, 2.62 mmol) in refluxing 6N HCl (5 mL) was added dropwise (E)-but-2-enal (367 mg, 5.24 mmol). The reaction was heated to reflux for 2 hours then cooled and neutralized with NH4OH. The aqueous phase was extracted with DCM, and the combined organic phases dried over MgSO4 and concentrated to yield 6-fluoro-8-methoxy-2-methylquinoline (500 mg, 99.8% yield) as a brown solid.

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 2 hours
  3. temperaturethen cooled
  4. extractionThe aqueous phase was extracted with DCM
  5. dry with materialthe combined organic phases dried over MgSO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-97f0201d046e46628db53f5726e91390
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889704B2

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