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

HRID 1517474Notes

Reaction equation

[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[N:12])=[N:9][CH:10]=1)(=[O:4])=[O:3].C(O)C.[ClH:16]>[Pd].O>[ClH:16].[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][NH2:12])=[N:9][CH:10]=1)(=[O:4])=[O:3]

Participants

Conditions

Temperature: 25 °C

Procedure

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+).

Workup

filtrationThe mixture was filtered through Celite
washwashed with water (1.8 L, 0.6 rel vol)
concentrationThe reaction mixture was concentrated under reduced pressure and ethanol (30.0 L, 10 rel vol)
additioncharged
temperatureThe mixture was cooled
stirringstirred
filtrationthe product collected by filtration
washThe solid was washed with ethanol (16.9 L, 5.6 rel vol)
customthe solid dried to constant weight

Sources & evidence

ORD record: ord-bf6e4b4d17d44bbcae94027d50081885
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232296B2

Reaction notes

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