Ammonia → 1H-Imidazo[4,5-c]quinoline-2,4-diamine, 1-(2-methylpropyl)-

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Reaction Conditions

Reaction Steps

4-Chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline-2-amine hydrobromide (8.61 g) and ammonia (131 mL of a 7 N solution in methanol) were added to a high-pressure vessel, which was sealed and heated overnight in an oven at 150° C. The resulting solution was concentrated under reduced pressure to provide 7 g of crude product. A portion of the product was purified by flash chromatography on silica gel (eluting with 3-4% methanol in dichloromethane with 1% ammonium hydroxide added.) The isolated product was washed with methanol, purified again by flash chromatography using the same conditions, and dried under high vacuum to provide 1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline-2,4-diamine as a gray, crystalline solid, mp >250° C. Anal. calcd. for C14H17N5: C, 65.68; H, 6.71; N, 27.43. Found: C, 65.69; H, 6.79; N, 27.42.

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