Reaktion #315721

Reaktionsgleichung

4-Chloro-6,7-dimethoxyquinoline

2′-hydroxyacetophenone

→

title compound

Ausbeute 43.0%

1-{2-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}-1-ethanone

Ausbeute 43.0%

Lösungsmittel

o-dichlorobenzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction solution was cooled to room temperature
2. 2
   Sonstigethe solvent was then removed
3. 3
   workup.DISTILLATIONby distillation under the reduced pressure
4. 4
   workup.ADDITIONChloroform was added to the residue
5. 5
   WaschenThe organic layer was washed with a 1 N aqueous potassium hydroxide solution and saturated brine
6. 6
   Trocknenwas dried over anhydrous sodium sulfate
7. 7
   SonstigeThe solvent was removed
8. 8
   workup.DISTILLATIONby distillation under the reduced pressure
9. 9
   Sonstigethe residue was purified by column chromatography

Vorschrift

4-Chloro-6,7-dimethoxyquinoline (58.1 mg), 2′-hydroxyacetophenone (361 mg), and 4-dimethylaminopyridine (317 mg) were suspended in o-dichlorobenzene (5 ml), and the suspension was stirred at 160° C. for 11 hr. The reaction solution was cooled to room temperature, and the solvent was then removed therefrom by distillation under the reduced pressure. Chloroform was added to the residue. The organic layer was washed with a 1 N aqueous potassium hydroxide solution and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by column chromatography using chloroform and by thin layer chromatography using acetone-hexane to give the title compound (36 mg, yield 43%).

Quelle