Hydrochloric Acid → 5-Chloroisoquinoline

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Reaction Steps

5-Aminoisoquinoline is reacted with hydrochloric acid, sodium nitrite and cuprous chloride to afford 5-chloroisoquinoline, which was then reduced with diborane in tetrahydrofuran. The resultant 5-chlorotetrahydroisoquinoline was then acetylated with acetic anhydride and chlorosulfonated with chlorosulfonic acid at low temperature, for example -50° C., to afford the desired chlorosulfonyl tetrahydroisoquinoline.

Provenance & Evidence