4-Chloro-6,7-dimethoxyquinoline → 4-(5,6-Dimethyl-2-phenyl-pyridin-3-yloxy)-6,7-dimethoxy-quinoline

Temperature

140 °C

1,2-Dichlorobenzene (4.5 ml) was added to 5,6-dimethyl-2-phenyl-pyridin-3-ol (267 mg), 4-chloro-6,7-dimethoxyquinoline (100 mg), and 4-(N,N-dimethylamino)pyridine (164 mg), and the mixture was stirred at 140° C. for 8 hr. The reaction solution was cooled to room temperature, and the solvent was then removed by distillation under the reduced pressure. Water was 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 by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using hexane-acetone to give the title compound (159 mg, yield 92%).

1. temperatureThe reaction solution was cooled to room temperature
2. customthe solvent was then removed by distillation under the reduced pressure
3. additionWater was added to the residue
4. extractionthe mixture was extracted with chloroform
5. washThe chloroform layer was washed with water
6. dry with materialwas dried over anhydrous sodium sulfate
7. customThe solvent was removed by distillation under the reduced pressure
8. customthe residue was purified by thin layer chromatography

ORD record

ord-f27b737fd7d84b73ab261a8331b9196a

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07560558B2