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

Participants

Reaction Steps

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 (300 mL×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).

Provenance & Evidence