Ethanol → N-(2-ethyl-1,2,3,4-tetrahydro-5-isoquinolinyl)acetamide

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A solution of 5-nitroisoquinoline (25 g, 0.144 mol) in 250 mL of EtOH was treated with iodoethane (26.9 g, 0.172 mol) and the resulting solution heated at reflux for 24 hours. The reaction mixture was cooled and the material which formed was collected and dried. The material obtained was converted to the title compound by the procedures described in Example 1. A white solid was obtained (4.42 g, 17%).

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