Reaktion #315807

Reaktionsgleichung

4-Chloro-6,7-dimethoxyquinoline

ethyl 6-methylsalicylate

→

title compound

Ausbeute 91.3%

Ethyl 2-[(6,7-dimethoxy-4-quinolyl)oxy]-6-methylbenzoate

Ausbeute 91.3%

Lösungsmittel

o-dichlorobenzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGwas further stirred at 140° C. for 2 hr
2. 2
   TemperaturThe reaction solution was cooled to room temperature
3. 3
   Sonstigethe solvent was removed by distillation under the reduced pressure
4. 4
   workup.ADDITIONWater was then added to the residue
5. 5
   Extraktionthe mixture was extracted with chloroform
6. 6
   WaschenThe chloroform layer was washed with water
7. 7
   Trocknenwas dried over anhydrous sodium sulfate
8. 8
   SonstigeThe solvent was removed
9. 9
   workup.DISTILLATIONby distillation under the reduced pressure
10. 10
    Sonstigethe residue was purified by column chromatography

Vorschrift

4-Chloro-6,7-dimethoxyquinoline (112 mg), ethyl 6-methylsalicylate (360 mg), and 4-dimethylaminopyridine (244 mg) were suspended in o-dichlorobenzene (1 ml), and the suspension was stirred at 120° C. overnight and was further stirred at 140° C. for 2 hr. The reaction solution was cooled to room temperature, and the solvent was removed by distillation under the reduced pressure. Water was then added to the residue, and the mixture was extracted with chloroform. The chloroform layer was washed with water 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 acetone-hexane to give the title compound (168 mg, yield 91%).

Quelle