4-Toluenesulfonyl chloride → HCID 57447011, compound

Participants

Reaction Steps

4-(2-Propyl-1H-imidazo[4,5-c]quinolin-1-yl)butanamide (2.90 g, 9.78 mmol) was treated with mCPBA (5.5 g, 25 mmol), concentrated ammonium hydroxide (100 mL of 29%), and p-toluenesulfonyl chloride (2.80 g, 14.7 mmol) according to the method described in Part E of Example 3. After the reaction solution was dried with potassium carbonate, it was decanted, and charcoal (2 g) was added. The mixture was heated at reflux for two hours, filtered through a layer of CELITE filter agent, and concentrated under reduced pressure. The crude solid was purified by column chromatography on silica gel (eluting with 90:10 dichloromethane:methanol) and combined with material from another run. The solid was recrystallized from 5:1 toluene:methanol (18 mL), dried overnight in a vacuum oven, recrystallized from ethanol:water, and dried overnight in a vacuum oven to provide 4-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butanamide as a tan solid, mp 249-251° C.

Provenance & Evidence