4-Toluenesulfonyl chloride → 8,9,10,11-Tetrahydro[1,2]oxazepino[2',3':1,2]imidazo[4,5-c]quinolin-6-amine

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Reaction Steps

A solution of 8,9,10,11-tetrahydro[1,2]oxazepino[2′,3′:1,2]imidazo[4,5-c]quinoline 5-oxide (0.1384 g, 0.5421 mmol) in 6 mL of dichloromethane was treated with 3 mL of concentrated aqueous NH4OH solution. The mixture was stirred rapidly and then p-toluenesulfonyl chloride (0.12 g, 0.65 mmol) was carefully added. Rapid stirring was continued for 40 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. The solid was triturated with ether and filtered. Crystallization from acetonitrile gave 0.0369 g of 8,9,10,11-tetrahydro[1,2]oxazepino[2′,3′:1,2]imidazo[4,5-c]quinolin-6-amine as a white powder, dec. 247-255° C. MS (APCI) m/z 255 (M+H)+; Anal. calcd for C14H14N4O: C, 66.13; H, 5.55; N, 22.03. Found: C, 65.82; H, 5.27; N, 22.11.

Provenance & Evidence