135838-04-9

3054-95-3

53981-24-1

135838-04-9

GENERAL PROCEDURE: A 1N HCl solution (82.5 mL) was added to 2-amino-5-fluorophenol (~1 mmol) in a round bottom flask. Acrolein diethyl acetal (2.5 mmol) was added to the reaction mixture. The resulting solution was refluxed at 111 °C for 24 hours. Upon completion of the reaction, the mixture was cooled to room temperature and neutralized to pH 7-8 by the addition of solid Na2CO3. Subsequently, the product was extracted with dichloromethane (3 x 100 mL), the organic layers were combined and dried with anhydrous Na2SO4. After removal of the solvent by evaporation under reduced pressure, the crude product was purified by column chromatography with the eluent being a mixture of 15% ethyl acetate/cyclohexane and methanol to give 6-fluoroquinolin-8-ol.