m-Chloroperbenzoic acid → HCID 18783935, compound

Participants

Reaction Steps

19.47 g (57.19 mmol) of 1-[4-(tert-Butoxycarbonylamino)butyl]-1H-imidazo[4,5-c]quinoline was dissolved in 500 ml of methylene chloride and 15.51 g (62.91 mmol) of 70% m-chloroperbenzoic acid was added thereto. The resulting mixture was stirred overnight at room temperature. A sodium hydrogencarbonate aqueous solution was added to the reaction mixture and the reaction mixture was extracted twice with chloroform. The organic phase was washed with brine and dried (Na2SO4). The solvent was distilled off under reduced pressure and the residue was purified by aluminum column chromatography (chloroform:methanol=50:1 to 10:1 (v/v)). Finally, the resulting product was triturated with diethyl ether and collected by filtration to obtain 15.88 g (44.55 mmol) of 1-[4-(tert-butoxycarbonylamino)butyl]-1H-imidazo[4,5-c]quinoline-5-oxide shown below as yellowish white powder. ##STR54## Its spectroscopic data are as follows: IR (KBr) cm-1 : 3280, 2970, 1710, 1540, 1365, 1250, 1170, 1140, 850, 760, 630.

Provenance & Evidence