4-Chloro-6,7-dimethoxyquinoline → HCID 22132734, compound

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Reaction Steps

Under argon, 2-furoyl 4-hydroxyphenyl ketone (205 mg) obtained in Example 129 and 4-dimethylaminopyridine (146 mg) were added to xylene (5 ml), and the admixture was stirred at room temperature for 1 hour. 4-Chloro-6,7-dimethoxyquinoline (244 mg) was added, and the admixture was then refluxed with heat for 20 hours. The reaction mixture was partitioned between saturated aqueous sodium hydrogen carbonate and chloroform, and the chloroform layer was 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 chloroform/ethyl acetate (5/1), to obtain 192 mg of the title compound (yield: 47%).

Provenance & Evidence