4-Toluenesulfonyl chloride → HCID 24852050, compound

Participants

Reaction Steps

A solution of 8,9-dihydroisoxazolo[2′,3′:1,2]imidazo[4,5-c]quinoline 5-oxide (0.0499 g, 0.220 mmol) in dichloromethane from the previous step was treated with 1.5 mL of concentrated aqueous NH4OH solution. The mixture was stirred rapidly and then p-toluenesulfonyl chloride (0.046 g, 0.242 mmol) was carefully added. Rapid stirring was continued for 5 minutes. The reaction mixture was then diluted with more dichloromethane, washed successively with dilute aqueous K2CO3, H2O and brine, dried over Na2SO4, and concentrated under reduced pressure. Chromatography (SiO2, 0-15% CMA/CHCl3) gave 0.015 g of 8,9-dihydroisoxazolo[2′,3′:1,2]imidazo[4,5-c]quinolin-6-amine as a brown solid, mp greater than 300° C.

Provenance & Evidence