4-Toluenesulfonyl chloride → HCID 57447048, compound

Participants

Reaction Steps

3-[2-(Ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propanamide (2.4 g, 8.1 mmol) was treated with mCPBA (3.24 g, 14.1 mmol) followed by ammonium hydroxide (40 mL) and p-toluenesulfonyl chloride (2.99 g, 15.7 mmol) according to a modification of the method described in Part D of Example 8. The reaction was not washed with 10% aqueous sodium hydroxide prior to the addition of ammonium hydroxide. After the amination reaction was stirred for two hours, 10% aqueous sodium hydroxide (25 mL) and saturated aqueous sodium bicarbonate (25 mL) were sequentially added with stirring. A precipitate formed and was isolated by filtration. The solid was triturated twice with 25% aqueous sodium hydroxide, isolated by filtration, washed with water, and dried in a vacuum oven for three days to provide 0.685 g of 3-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propanamide as tan needles, mp>250° C.

Provenance & Evidence