2-[1,2,4]triazol-1-yl-nicotinonitrile → 1-[2-(1H-1,2,4-Triazol-1-yl)pyridin-3-yl]methanamine

Participants

Reaction Steps

A catalytic amount of Raney 2800 nickel in water (Aldrich; withdrawn as a wet slurry with the tip of a spatula) was added under air to a translucent slurry of 2-[1,2,4]triazol-1-yl-nicotinonitrile (1.053 g, 6.16 mmol), as prepared in the previous step, in 2 M NH3/MeOH (50 mL). The flask was then sealed with a septum, the air was removed from the system, and the flask was flushed with H2 gas under balloon pressure. The reaction was stirred at rt under H2 for 11 h (TLC showed no starting material remained), and the bulk of the Raney nickel was then removed with a magnet. The translucent white reaction mixture was then diluted with DCM (50 mL), filtered, and the translucent filtrate was concentrated under vacuum to provide the title compound as a beige crystalline solid (988 mg, 92%).

Provenance & Evidence