4-METHOXYBENZAMIDINE, HYDROCHLORIDE

Off-White Crystalline Solid

A solution of 4-methoxybenzonitrile 2 (2.1 g, 15.7 mmol), sodium methylate (86 mg, 1.57 mmol) in 20 mL of anhydrous methanol was stirred at room temperature for 48 h. Then ammonium chloride (0.84 g, 15.7 mmol) was added, and the reaction group was stirred for another 24 h the precipitate was collected by filtration, washed with diethyl ether, and then dried in vacuum to obtain 3 as a white solid (1.3 g, 44.5percent), MS (ESI) m/z: 151.1 ([MH]).General procedure: The ethyl imidate hydrochloride 4 (10 mmol) was dissolved inethanol (10 mL) and placed in a round-bottomed flask equippedwith a magnetic stir bar. After sealing the flask with a rubberseptum ammonia in methanol (10 mL) was added to the reactionmixture using a syringe. The reaction mixture was stirred at roomtemperature for 24 h. After evaporation in vacuo, the crude productwas purified by flash column chromatography over silica gel(EtOAc/methanol4:1) to afford the amidine hydrochloride 1.4.3.2