4-Toluenesulfonyl chloride → HCID 16739230, compound

Participants

Reaction Steps

A solution of 9,10-dihydro-8H-[1,2]oxazino[2′,3′:1,2]imidazo[4,5-c]quinoline 5-oxide (0.364 g, 1.51 mmol) in 10 mL of dichloromethane was treated with 7 mL of concentrated aqueous NH4OH solution. The mixture was stirred rapidly and then p-toluenesulfonyl chloride (0.34 g, 1.78 mmol) was carefully added. Rapid stirring was continued for 2 hours. 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. The solid was dissolved in hot CH3CN. The resulting crystals were filtered off and dried to give 0.0578 g of 9,10-dihydro-8H-[1,2]oxazino[2′,3′:1,2]imidazo[4,5-c]quinolin-6-amine as a tan solid, dec. 229-234° C. MS (APCI) m/z 241 (M+H)+; Anal. calcd for C13H12N4O: C, 64.99; H, 5.03; N, 23.32. Found: C, 64.81; H, 4.74; N, 23.44.

Provenance & Evidence