Water → 1-(6-Hydroxy-3,4-dihydroisoquinolin-2(1H)-yl)ethan-1-one

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Reaction Steps

A mixture of 57.6 g of 1,2,3,4-tetrahydro-6-hydroxy-isoquinoline-hydrobromide, 22.6 g of anhydrous sodium acetate, and 76.6 g of acetic acid anhydride in 300 ml of methylene chloride is held at the boiling point for one hour under reflux. 300 ml of water are added thereto, the organic phase is separated, and the aqueous phase is extracted several times with methylene chloride. After evaporation of the methylene chloride extract, the residue is dissolved in dilute sodium hydroxide, stirred for 30 minutes on a boiling water bath, and the reaction product is precipitated by the introduction of carbon dioxide. The filtered substance is recrystallized from ethanol. 43.5 g of 2-acetyl-1,2,3,4-tetrahydro-6-hydroxy-isoquinoline are obtained. m.p. = 135° - 136° C. (ethanol - diisopropyl ether).

Provenance & Evidence