Ethyl orthoformate → 1-[3-(tert-butoxycarbonylamino)propyl]-4-chloro-1H-imidazo[4,5-c]quinoline

Participants

Reaction Conditions

Reaction Steps

0.36 ml (2.14 mmol) of triethyl ortho-formate was added to 0.15 g (0.428 mmol) of 3-amino-4-[3-(tert-butoxycarbonylamino)-propylamino]-2-chloro-quinoline. The mixture was stirred at 100° C. for 2 hours and then at 80° C. for overnight. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:methanol 150:1 to 100:1 (v/v)) to obtain 0.14 g (0.388 mmol) of 1-[3-(tert-butoxycarbonylamino)propyl]-4-chloro-1H-imidazo[4,5-c]quinoline shown below as white powder (mp: 155-156° C.). ##STR36## Its spectroscopic data are as follows: IR (KBr) cm-1 : 3380, 1680, 1520.

Provenance & Evidence