1,2,3,4-Tetrahydroisoquinoline → 2-(3-Nitropyridin-4-yl)-1,2,3,4-tetrahydroisoquinoline

Participants

Reaction Steps

Sodium hydride (60%, 386.4 mg, 9.66 mmol) was added at 0° C. to a solution of 1,2,3,4-tetrahydroisoquinoline (1.06 ml, 8.05 mmol) in N,N-dimethylformamide (30 ml) and stirred for 10 minutes at the same temperature. 4-Chloro-3-nitropyridine (1.124 g, 7.09 mmol) prepared in Step 1 was added to the reaction mixture, which was stirred for 2 hours at room temperature, diluted with a mixture of water (10 ml) and ethyl acetate (100 ml), and then washed with water (100 ml) twice. The separated organic layer was dried on anhydrous magnesium sulfate and concentrated under reduced pressure to give the titled compound as a yellow solid (1.13 g, 89.3%).

Provenance & Evidence