Stannous Chloride → 4-(Aminomethyl)benzonitrile hydrochloride

Temperature

60 °C

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).

1. washwashed with 1 N sodium bicarbonate, water and brine
2. dry with materialThe solution was then dried over MgSO4
3. concentrationconcentrated
4. dissolutionThis azide intermediate was dissolved in methanol
5. temperatureAfter warming to rt
6. stirringstirring for 0.5 h
7. concentrationthe reaction mixture was concentrated
8. additionCold 1 N NaOH was added
9. extractionthe mixture was extracted with CH2Cl2
10. dry with materialThe combined organic layers were dried over Na2SO4
11. concentrationconcentrated

ORD record

ord-ac3a90016833463b84bbc94fa8646f9a

Source dataset

uspto-grants-2002_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06399619B1