Réaction #315786

Équation de réaction

4-Chloro-6,7-dimethoxyquinoline

ethyl salicylate

→

title compound

Rendement 63.3%

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

Rendement 63.3%

Solvants

o-dichlorobenzene

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction solution was cooled to room temperature
2. 2
   Autrethe solvent was removed by distillation under the reduced pressure
3. 3
   workup.ADDITIONWater was then added to the residue
4. 4
   Extractionthe mixture was extracted with chloroform
5. 5
   LavageThe chloroform layer was washed with water
6. 6
   Séchagewas dried over anhydrous sodium sulfate
7. 7
   AutreThe solvent was removed
8. 8
   workup.DISTILLATIONby distillation under the reduced pressure
9. 9
   Autrethe residue was purified by column chromatography

Mode opératoire

4-Chloro-6,7-dimethoxyquinoline (100 mg), ethyl salicylate (336 mg), and 4-dimethylaminopyridine (244 mg) were suspended in o-dichlorobenzene (1 ml), and the suspension was stirred at 120° C. overnight. 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 (100 mg, yield 56%).

Source