2-(methylsulfonyl)-5-nitropyridine → 6-(Methanesulfonyl)pyridin-3-amine

HRID 2387291Notes

Reaction equation

HRID 2387291 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][N:6]=1)(=[O:4])=[O:3]>[OH-].[OH-].[Pd+2].CO.C(OCC)(=O)C>[CH3:1][S:2]([C:5]1[N:6]=[CH:7][C:8]([NH2:11])=[CH:9][CH:10]=1)(=[O:4])=[O:3]

Participants

5

Reactant 1

HCID 12115522-(methylsulfonyl)-5-nitropyridine

Product 1

HCID 200389776-(Methanesulfonyl)pyridin-3-amineYield 86.3%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 241 mg (0.34 mmol) of 20% of Pearlman's catalyst on carbon and 693 mg (3.43 mmol) of the 2-methanesulfonyl-5-nitropyridine in 15 mL of MeOH and 3 mL of ethyl acetate was stirred under an atmosphere of hydrogen for 3 hours. The solution was filtered and concentrated. The crude mixture was further purified by filtration through a silica column with ethyl acetate to afford 510 mg (86%) of 6-methanesulfonylpyridin-3-ylamine.

Workup

  1. filtrationThe solution was filtered
  2. concentrationconcentrated
  3. filtrationThe crude mixture was further purified by filtration through a silica column with ethyl acetate

Sources & evidence

ORD record
ord-72ec3877116849b0b5ca26730ab50cd9
Source dataset
uspto-grants-2012_09
Patent number
US08268859B2

Reaction notes

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