4-Chloro-6,7-dimethoxyquinoline → HCID 22132765, compound

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Reaction Steps

Under argon, 4-hydroxyphenyl 2-methylphenyl ketone (1.334 g) obtained in Example 126 and 4-dimethylaminopyridine (845 mg) were added to xylene (15 ml), and the admixture was stirred at room temperature for 1 hour. 4-Chloro-6,7-dimethoxyquinoline (1.406 g) was added, and the admixture was refluxed with heat for 23 hours. The reaction mixture was partitioned between saturated aqueous sodium hydrogen carbonate and chloroform, and the chloroform layer was then dried with anhydrous magnesium sulfate. After removing the solvent by reduced-pressure distillation, the resulting residue was purified by chromatography on silica gel eluting with hexane/ethyl acetate and then with chloroform, followed by thin layer chromatography on silica gel eluting with hexane/acetone (2/1), to obtain 1.258 g of the title compound (yield: 50%).

Provenance & Evidence