Ammonia → 3,5-Dimethoxy-benzamidine

Participants

Reaction Steps

Dry HCl gas was bubbled through a cooled (−15° C.) solution of 3,5-dimethoxybenzonitrile (1.50 g, 9.20 mmol) for 30 minutes. The reaction mixture was placed in a refrigerator overnight. After evaporation of the solvent, a white solid was obtained which was dissolved in ethanol. 9.2 ml of a 2 molar solution of ammonia in Methanol was added and the reaction mixture was stirred at room temperature overnight. After evaporation of the solvent, the title compound, MS: m/e=181.2 (M+H+), (1.21 g, 71%) was obtained by chromatographic purification of the residue (silica gel, MeOH, DCM). 1H-NMR (300 MHz, d6-DMSO, 25° C.): δ(ppm)=3.80 (6H, s), 6.82 (1H, t, J=2 Hz), 7.05 (2H, t, J=2 Hz), 9.35 (3H, bs).

Provenance & Evidence