Ammonium Hydroxide → 5-(Aminomethyl)pyridin-2-amine

To a solution of 6-aminonicotinonitrile 117-A (5.0 g, 42 mmol) was added a solution of 1 M BH3-THF (294 mL, 294 mmol) at 0° C. (prepared as in J.Org. Chem., Vol. 38, No. 5, 1973). The reaction was stirred at room temperature for 1 hour. The reaction mixture was then slowly pored into ice water. 100 mL 4N HCl was added and stirred for 20 min. The solution was basified with NH4OH to pH of about 11, and then concentrated. THF (300mL×2) was added to the mixture followed by addition of solid KOH (excess). The suspension was stirred. The THF layer was collected by filtration and concentrated to give 5-(aminomethyl)pyridin-2-amine 117-B (4.3 g).

1. customprepared as in J.Org
2. stirringstirred for 20 min
3. concentrationconcentrated
4. additionTHF (300mL×2) was added to the mixture
5. additionfollowed by addition of solid KOH (excess)
6. stirringThe suspension was stirred
7. filtrationThe THF layer was collected by filtration
8. concentrationconcentrated

ORD record

ord-dc84e24aea9d480893515ad0ec3b381a

Source dataset

uspto-grants-2008_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07381824B2