Water → 3-(Aminomethyl)-5-chloropyridine

Participants

Reaction Steps

A mixture of 5-chloro-nicotinonitrile (63.8 mg, 461 μmol), 2-propanol (9.2 mL; not dry), and CaSO4 (−325 mesh) (920 mg, 6.76 mmol) was treated with a suspension of Raney Cobalt 2700 in 2-propanol under air (2 mL) (prepared by diluting 2 mL of the commercial water slurry with 15 mL 2-propanol, centrifuging, decanting, and repeating with 2×15 mL 2-propanol, then resuspending with 2 mL 2-propanol). The flask was then sealed and evacuated until bubbles formed, and the evacuated flask was flushed with H2 gas via balloon pressure. After 11 h stirring at rt under balloon H2 pressure, a NMR spectrum of a worked-up reaction aliquot indicated 80% conversion to the title compound. The reaction was then filtered, the filter cake was washed with 2-propanol (3×10 mL), and the combined clear colorless filtrates were concentrated briefly under rotary evaporation at 50° C. The residue was taken up in DCM and concentrated again to afford the volatile crude title compound (53 mg, 81%).

Provenance & Evidence