Ethanol → 2-(6-Fluoroquinolin-2-yl)ethanol

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6-Fluoro-2-methylquinoline (1.00 g, 6.20 mmol) and sodium hydroxide were each added sequentially to the mixture of HCHO in water. Then 2 mL of EtOH were added to the mixture. The resulting solution was stirred at about 85° C. overnight. The organic layer was extracted with EA (3×10 mL), collected and dried with anhydrous Na2SO4, filtered and concentrated to afford a pink oil. The crude material was purified by chromatography on silica-gel (eluent: PE/EA=6/1) and then further purified by combi-flash chromatography (NH4HCO3/H2O, MeOH/H2O=40%-60%) to give 360 mg of the title product (yield: 30.3%).

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