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

Participants

Reaction Steps

To 5-Methanesulfonyl-pyridine-2-carbonitrile (22 kg, 1.0 mol eq, limiting reagent) was charged palladium on carbon (2.0 kg, 5% w/w), ethanol (110 L, 5 rel vol), water (14 L, 0.64 rel vol) and hydrochloric acid (25.04 kg, 32% w/w). An ethanol line rinse (16 L, 0.7 rel vol) followed. The reaction mixture was heated and subjected to an atmosphere of hydrogen until the reaction was complete as judged by HPLC analysis. Water (108 L, 4.9 rel vol) was charged, the catalyst filtered off and washed with water (36 L, 1.6 rel vol). The combined filtrates were concentrated under reduced pressure to approximately 2.5 rel vols. The reaction was then heated and ethanol (126.3 L, 5.7 rel vol) was charged. The reaction mixture was cooled, stirred and isolated by filtration. The solid was washed with ethanol (73.7 L, 3.3 rel vol) and dried to constant weight to yield the title compound (20.1 kg, 9.05 mol, 82%).

Provenance & Evidence