Stannous Chloride → 4-(Aminomethyl)benzonitrile hydrochloride

Participants

Reaction Conditions

Reaction Steps

4-Cyanobenzyl bromide (5.0 g, 26 mmol) was dissolved in dimethylformamide. Sodium azide (3.3 g, 50 mmol) was added and the reaction mixture was stirred at 60° C. for 1 h. The mixture was diluted with ether and washed with 1 N sodium bicarbonate, water and brine. The solution was then dried over MgSO4 and concentrated. This azide intermediate was dissolved in methanol and added to a slurry of SnCl2 (7.4 g, 39 mmol) in methanol at 0° C. After warming to rt and stirring for 0.5 h, the reaction mixture was concentrated. Cold 1 N NaOH was added and the mixture was extracted with CH2Cl2. The combined organic layers were dried over Na2SO4 and concentrated to afford the title compound. 1H-NMR (300 MHz, CD3OD) δ4.11 (s, 2 H), 7.63 (d, J=8, 2 H), 7.82 (d, J=8, 2 H).

Provenance & Evidence