Ammonia → 1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-2-methyl-1H-imidazo[4,5-c]quinolin-4-amine

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Reaction Steps

4-Chloro-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-2-methyl-1H-imidazo[4,5-c]quinoline (2.307 g, 5.873 mmol) was treated according to the method described in Part B of Example 27 using 60 mL of 7 N ammonia in methanol. Following the purification steps, the solid product was stirred for 16 hours in 25% potassium hydroxide in ethanol, isolated by filtration, washed with water and isopropyl alcohol, and dried. The resulting white solid was stirred for one hour with 6 N hydrogen chloride in ethanol, and the mixture was then adjusted to pH 14 with the addition of 6 N potassium hydroxide. The solid was isolated by filtration, washed with water and diethyl ether, and dried under high vacuum at 100° C. for 18 hours to provide 1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-2-methyl-1H-imidazo[4,5-c]quinolin-4-amine as a white powder, mp 294.0-296.0° C.

Provenance & Evidence