Sodium Iodide → HCID 67916452, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of 2-(methylaminomethyl)quinoline, prepared by the procedure of Example 3, Step 1, (3.67 g, 21.35 mmol), sodium iodide (2.78 g, 18.56 mmol), and potassium carbonate (3.08 g, 138.21 mmol) in acetonitrile (80 mL) was added 3-chloropropyl-4-nitrophenyl ether (4.00 g, 18.56 mmol). The mixture was stirred at 80° C. overnight, concentrated and partitioned between 10% K2CO3 and ethyl acetate. The organic phase was washed with brine, dried (MgSO4), and concentrated to afford an oil. The product was purified by HPLC (10% MeOH/CH2Cl2) to afford 2.34 g (36%) of pure product as a yellow oil.

Provenance & Evidence