Hydrochloric Acid → Isoquinoline, 6-hydroxy-1,2,3,4-tetrahydro-, hydrochloride

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Reaction Steps

In dimethyl sulfide (20 ml), 6-methoxy-1,2,3,4-tetrahydroisoquinoline (7.75 g) was dissolved. Under ice cooling, aluminum chloride (19.0 g) was added to the resulting solution, followed by stirring at room temperature for 3 hours. Dichloromethane and dilute hydrochloric acid were added to separate the water layer. The water layer was made basic by the addition of a saturated aqueous solution of sodium bicarbonate, followed by extraction with dichloromethane. The extract was dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was dissolved in saturated solution of hydrochloride in ethanol (100 ml). To the residue obtained by distilling off the solvent under reduced pressure, ethyl acetate was added. The solid thus precipitated was collected by filtration, whereby the title compound (7.91 g, 90%) was obtained.

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