Thionyl Chloride → 3-(Chloromethyl)isoquinoline hydrochloride

Participants

Reaction Conditions

Reaction Steps

3-Hydroxymethylisoquinoline (110 g) is added to thionyl chloride (130 cc), whilst cooling so as to keep the temperature between 25° and 30° C. The reaction mixture is then heated to the reflux temperature at a rate which is such that the evolution of gas is not excessive. The mixture is heated under reflux for 90 minutes (until the evolution of gas ceases), and then for a further 30 minutes. It is then cooled to 5° C. with ice, the slurry formed is filtered and the solid is washed with diethyl ether. 3-Chloromethylisoquinoline hydrochloride (136 g), melting at 202° C., is obtained.

Provenance & Evidence