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

HRID 1517475Notes

Reaction equation

HRID 1517475 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

6

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 591699295-(Methylsulfonyl)pyridine-2-carbonitrile

Product 1

HCID 66725223[5-(Methanesulfonyl)pyridin-2-yl]methanaminium chlorideYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

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%).

Workup

  1. washAn ethanol line rinse (16 L, 0.7 rel vol)
  2. temperatureThe reaction mixture was heated
  3. additionWater (108 L, 4.9 rel vol) was charged
  4. filtrationthe catalyst filtered off
  5. washwashed with water (36 L, 1.6 rel vol)
  6. concentrationThe combined filtrates were concentrated under reduced pressure to approximately 2.5 rel vols
  7. temperatureThe reaction was then heated
  8. additionethanol (126.3 L, 5.7 rel vol) was charged
  9. temperatureThe reaction mixture was cooled
  10. customisolated by filtration
  11. washThe solid was washed with ethanol (73.7 L, 3.3 rel vol)
  12. customdried to constant weight

Sources & evidence

ORD record
ord-2c59dadcfc81430ead672d280b550fa9
Source dataset
uspto-grants-2012_07
Patent number
US08232296B2

Reaction notes

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