N,N'-Dimethylethylenediamine → 3,4-Dimethoxybenzonitrile

Participants

Reaction Conditions

Reaction Steps

An oven dried screw cap test tube was charged with NaCN (107 mg, 2.184 mmol), dried KI (60 mg, 0.361 mmol, 20 mol %) and CuI (34 mg, 0.210 mmol, 10 mol %), evacuated and backfilled with argon three times. 1-Bromo-3,4-dimethoxybenzene (260 μL, 1.807 mmol), N,N′-dimethylethylenediamine (195 μL, 1.832 mmol) and anhydrous toluene (1.2 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 complete conversion of starting material with formation of the title product (confirmed by GC-MS).

Provenance & Evidence