4-Chloro-6,7-dimethoxyquinoline → HCID 22132803, compound

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Reaction Steps

Under argon, 4-hydroxyphenyl 4-iodophenyl ketone (380 mg) obtained in Example 177 and 4-dimethylaminopyridine (158 mg) were added to xylene (11 ml), and the admixture was stirred at room temperature. After 2 hours, 4-chloro-6,7-dimethoxyquinoline (262 mg) was added, and the admixture was refluxed with heat overnight. 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/ethyl acetate, followed by thin layer chromatography on silica gel eluting with chloroform/ethyl acetate (5/1), to obtain 459 mg of the title compound (yield: 77%).

Provenance & Evidence