N,N'-Dimethylethylenediamine → 2,5-Dimethylbenzonitrile

Participants

Reaction Conditions

Reaction Steps

An oven dried screw cap test tube was charged with NaCN (93 mg, 1.898 mmol), dried KI (52 mg, 0.313 mmol, 20 mol %) and CuI (30 mg, 0.158 mmol, 10 mol %), evacuated and backfilled with argon three times. 2-Bromo-1,4-dimethylbenzene (215 μL, 1.557 mmol), N,N′-dimethylethylenediamine (165 μL, 1.549 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 washed with 1 mL of water and dried over MgSO4. The GC analysis showed consumption of the majority of the starting material, and formation of the title compound (as confirmed by GC-MS).

Provenance & Evidence