Potassium Hydroxide → 6-Methoxy-1,2,3,4-tetrahydroisoquinoline

Participants

Reaction Steps

6-Methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (41 g) was dissolved in H2O, basified with aqueous KOH solution and extracted with CHCl3. The CHCl3 extracts were dried over MgSO4 and evaporated to dryness to yield 33 g of 6-methoxy-1,2,3,4-tetrahydroisoquinoline base (0.2M). The base (33 g, 0.2M) and Palladium Black (1.5 g) were mixed together and heated at 160°-190° C. for 6 hours. The cooled reaction mixture was extracted with MeOH and the Palladium Black was filtered off. The MeOH was evaporated to dryness and the residue was chromatographed in CHCl3 on silica gel column. Fractions containing product were combined and evaporated to yield 6-methoxyisoquinoline as an oil (16 g, 50%).

Provenance & Evidence