N,N'-Dimethylethylenediamine → 3-Quinolinecarbonitrile

Participants

Reaction Conditions

Reaction Steps

An oven dried screw cap test tube was charged with NaCN (98 mg, 2.0 mmol), dried KI (32 mg, 0.168 mmol, 20 mol %) and CuI (56 mg, 0.337 mmol, 10 mol %), evacuated and backfilled with argon three times. 3-Bromoquinoline (225 μL, 1.66 mmol), N,N′-dimethylethylenediamine (180 μL, 1.69 mmol) and anhydrous toluene (1 mL) were added under argon. The tube was sealed and the reaction mixture was stirred magnetically at 110° C. for 24 h. The resulting yellow suspension was cooled to room temperature, 2 mL of ethyl acetate, 1 mL of ammonium hydroxide (30%) and 1 mL of water were added. The mixture was stirred at 25° C. for 10 min, then the organic layer was separated and the aqueous layer was extracted three times with ethyl acetate (3×2 mL). The combined organic layers were washed with 5 mL of water and dried over MgSO4. The solvent was removed at reduced pressure. Purification of the residue by flash chromatography on silica gel (2×15 cm; hexane/ethyl acetate 10:1) provided 188 mg (74% yield) of the title compound as a white solid.

Provenance & Evidence