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ChemicalBook CAS DataBase List 5-Fluoro-8-methoxyquinoline

5-Fluoro-8-methoxyquinoline synthesis

3synthesis methods
-

Yield:439-88-3 16 %

Reaction Conditions:

with hydrogenchloride in water at 110;Inert atmosphere;

Steps:

106 Synthesis of 5-fluoro-7-nitroquinoline-8-ol (106)

At room temperature, 5-fluoro-2-methoxyaniline (68a) (1.0 g, 7.08 mmol) was addedHydrochloric acid (6.0M) (10.0mL), the reaction mixture was heated to 110°C,Slowly add inAcrolein diethyl acetal(2.31g, 17.7mmol),Stir for 2 hours,Cool to room temperature, and adjust the pH value of the aqueous phase to about 7-8 with saturated potassium carbonate aqueous solution.The resulting mixture was extracted with ethyl acetate (50.0 mL x 3),The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure.The resulting residue was subjected to silica gel column chromatography(gradient elution, eluent: petroleum ether/ethyl acetate=7/1-4/1) purification,5-Fluoro-8-methoxyquinoline (106a) was obtained (0.20 g, 16% yield).

References:

WO2022/253152,2022,A1 Location in patent:Page/Page column 48; 121