4-Toluenesulfonyl chloride → HCID 10314366, compound

Participants

Reaction Steps

A solution of 2-ethoxymethyl-1-(morpholin-4-yl)-1H-imidazo[4,5-c]quinoline (1.61 g, 5.51 mmol) in 40 mL of CH2Cl2 was treated with MCPBA (1.78 g, 6.70 mmol, 77% max). After 30 min, the reaction mixture was treated with 20 mL of concentrated NH4OH solution and p-toluenesulfonyl chloride (1.03 g, 5.41 mmol). After 15 min, the reaction mixture was diluted with CH2Cl2 and water and the phases were separated. The organic portion was washed with 5% Na2CO3 solution, water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure to yield a tan foam. Chromatography (SiO2, 97:3 CHCl3:MeOH) gave a light yellow foam. The foam was triturated with diethyl ether and filtered to give 2-ethoxymethyl-1-(morpholin-4-yl)-1H-imidazo[4,5-c]quinolin-4-amine (0.794 g) as a light cream colored solid. mp 223–224° C.;

Provenance & Evidence