Sodium hydride → 4-[2-(4-Chlorophenyl)ethoxy]-8-fluoroquinoline

HRID 1196475

Reaktionsgleichung

Reaktionsgleichung von HRID 1196475
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][OH:12])=[CH:6][CH:5]=1.Cl[C:14]1[C:23]2[C:18](=[C:19]([F:24])[CH:20]=[CH:21][CH:22]=2)[N:17]=[CH:16][CH:15]=1>CN(C=O)C>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][O:12][C:14]2[C:23]3[C:18](=[C:19]([F:24])[CH:20]=[CH:21][CH:22]=3)[N:17]=[CH:16][CH:15]=2)=[CH:6][CH:5]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 74647p-Chlorophenethylic alcoholHCID 27365874-Chloro-8-fluoroquinoline

Produkt 1

HCID 190940614-[2-(4-Chlorophenyl)ethoxy]-8-fluoroquinolineAusbeute 11,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To 1.2 g of sodium hydride in 50 mL of DMF was added 3.9 g of 2-(4-chlorophenyl)ethyl alcohol. The mixture was stirred at room temperature for one hour, then 4.5 g of 4-chloro-8-fluoroquinoline in 10 mL of DMF was added, the mixture was heated to reflux for two hours. Then the mixture was allowed to cool to room temperature while it was stirred for four hours, after which it was poured into an ice/water mixture. The mixture was filtered, and the filter cake was washed with H2O. Recrystallization from pentane/ethyl acetate gave 0.840 g of the title product. Yield 11.2%. M.P. 139°-140° C.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for two hours
  3. temperatureto cool to room temperature while it
  4. stirringwas stirred for four hours
  5. filtrationThe mixture was filtered
  6. washthe filter cake was washed with H2O
  7. customRecrystallization from pentane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-ca708ebc3ca04d56a05d79fab839dc38
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05114939

Verknüpfte Notizen

Wird geladen…