Ammonia → 3-(methylsulfonyl)-2-Pyridinamine

HRID 2238690Notes

Reaction equation

HRID 2238690 reaction equation
Cl[C:2]1[C:7]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH3:12]>>[CH3:11][S:8]([C:7]1[C:2]([NH2:12])=[N:3][CH:4]=[CH:5][CH:6]=1)(=[O:10])=[O:9]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 125137462-Chloro-3-(methanesulfonyl)pyridine

Product 1

HCID 669270783-(methylsulfonyl)-2-Pyridinamine

Procedure

The mixture of 800 mg of 2-chloro-3-(methylsulfonyl)pyridine (synthesized according to a method disclosed in J. Org. Chem. 1979, 44, 3080-3082) and 60 mL of aqueous ammonia, was stirred overnight in a sealed-tube at 175° C. After cooling back to room temperature, the mixture was extracted with diethyl ether, and the organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The insolubles were filtered. The filtrate was concentrated under reduced pressure, and 473 mg of 3-(methylsulfonyl)pyridine-2-amine [162-1] was obtained as a light orange solid.

Workup

  1. customsynthesized
  2. extractionthe mixture was extracted with diethyl ether
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe insolubles were filtered
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e2b814373a2f4e0b98e1d0b66e74486b
Source dataset
uspto-grants-2010_05
Patent number
US07718801B2

Reaction notes

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