Ammonium Hydroxide → 5-(Methylsulfonyl)pyridin-3-amine

HRID 538836Notes

Reaction equation

HRID 538836 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:7]=1.[OH-].[NH4+:13]>[O-]S([O-])(=O)=O.[Cu+2]>[CH3:11][S:8]([C:6]1[CH:7]=[C:2]([NH2:13])[CH:3]=[N:4][CH:5]=1)(=[O:10])=[O:9]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 223919813-Bromo-5-(methylsulfonyl)pyridine

Product 1

HCID 592146735-(Methylsulfonyl)pyridin-3-amineYield 31%

Reagents, catalysts & solvents 1

HCID 24462Copper SulfateCatalyst

Procedure

A mixture of 3-bromo-5-(methylsulfonyl)pyridine (0.50 g, 2.1 mmol) and CuSO4.(H2O)5 (53 mg, 0.21 mmol) in concentrated ammonium hydroxide (3 mL) was heated in a sealed tube at 170° C. for 16 hours. The reaction was cooled to room temperature and extracted with ethyl acetate. The combined extracts were dried over sodium sulfate and evaporated to give a brown solid. The solid was purified by column chromatography on silica gel using 0-5% MeOH in dichloromethane to give 5-(methylsulfonyl)pyridin-3-amine (0.11 g, 31% yield) as a tan solid. LC/MS: m/z 173.3 (M+H)+ at 0.21 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined extracts were dried over sodium sulfate
  3. customevaporated
  4. customto give a brown solid
  5. customThe solid was purified by column chromatography on silica gel using 0-5% MeOH in dichloromethane

Sources & evidence

ORD record
ord-227880e5d77f4bb69a47ee693ea90f6e
Source dataset
uspto-grants-2014_10
Patent number
US08865771B2

Reaction notes

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