Hydrochloric Acid → 1-Methyl-5,6,7,8-tetrahydroisoquinoline

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Reaction Steps

A solution of 1-methylisoquinoline (1.0 g) in methanol (30 ml) was saturated with gaseous hydrogen chloride at room temperature. The mixture was treated with platinum(IV) oxide (0.2 g). The mixture was vigorous stirred under hydrogen atmosphere at room temperature until hydrogen absorption was stopped. The reaction mixture was filtered off to remove the catalyst. The filtrate was concentrated in vacuo and the residue was taken up with water. The mixture was alkalized with sodium carbonate and the resultant precipitate was extracted with isopropyl ether. The extracts were dried over sodium sulfate, filtered and concentrated in vacuo to give 1-methyl-5,6,7,8-tetrahydroisoquinoline (1.03 g) as a brown oil. 1H NMR (CDCl3, δ): 1.6-2.0 (4H, m), 2.42 (3H, s), 2.5-2.9 (4H, m), 6.82 (1H, m), 8.16 (1H, m)

Provenance & Evidence