Chloroform → HCID 131715687, compound

Participants

Reaction Steps

A solution of 5.00 g (17.15 mmol) of (±) N-(4,5,5a,6,7,8-hexahydro-6-methylthiazolo[4,5-f]quinolin-2-yl)-2-methylpropanamide (Example 15) in 150 ml of chloroform containing 20.6 ml (19.25 mmol) of a 1.07 M solution of cyanogen bromide in chloroform is refluxed, under nitrogen, for 12 hours. The solution is concentrated and the resultant yellow oily solid is refluxed in 150 ml of 10% hydrochloric acid for 12 hours. The solution is cooled, basified with ammonium hydroxide and extracted into chloroform. The chloroform extract is dried (magnesium sulfate), filtered and concentrated to a brown oil. Medium pressure chromatography (silica gel, 5% methanol--2% ammonium hydroxide--93% ethyl acetate) followed by salt formation and recrystallization from methanol/diethyl ether affords the title compound as a tan solid; mp 277°-279° C. (dec.).

Provenance & Evidence