Hydrochloric Acid → [5-(Methanesulfonyl)pyridin-2-yl]methanaminium chloride

Participants

Reaction Conditions

Reaction Steps

To 5-methanesulfonyl-pyridine-2-carbonitrile (3.0 kg, 1 mol eq, limiting reagent) was charged absolute ethanol (30.7 L, 10 rel vol), 32% aqueous 6 M hydrochloride acid (3.9 kg, 2 mol eq) and palladium on carbon (303 g, 1.50 g, 10% w/w). The reaction was stirred under a hydrogen atmosphere (2.5 bar) at 25° C. until the reaction was complete as judged by HPLC analysis. Water (5.4 L, 1.8 rel vol) was charged. The mixture was filtered through Celite and washed with water (1.8 L, 0.6 rel vol). The reaction mixture was concentrated under reduced pressure and ethanol (30.0 L, 10 rel vol) charged. The mixture was cooled, stirred and the product collected by filtration. The solid was washed with ethanol (16.9 L, 5.6 rel vol) and the solid dried to constant weight yielding the title compound (3.1 kg, 13.8 mol, 84%); 1H NMR (d6-DMSO): 9.10 (d, 1H, J=2.4 Hz), 8.73 (br s, 3H), 8.41 (dd, 1H, J 2.4, 8.3 Hz), 7.82 (d, 1H, J=8.2 Hz), 4.30-4.34 (m, 2H), 3.35 (s, 3H) ppm; LCMS: m/z 187.3 (MH+).

Provenance & Evidence