Hydrogen Peroxide → HCID 22336280, compound

HRID 586800Notes

Reaction equation

HRID 586800 reaction equation
[OH:1]O.[C:3]([NH:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[OH-].[Na+]>FC(F)(F)C(O)=O>[C:3]([NH:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N+:11]=1[O-:1])=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 22336268HCID 22336268, compound

Product 1

HCID 22336280HCID 22336280, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Thirty-one percent aqueous hydrogen peroxide (1.0 ml) was added to a solution of N-t-butyl-5-chloro-2-pyridinecarboxamide obtained in Example 40 (0.35 g, 1.65 mmol) in trifluoroacetic acid (5 ml), and heated under reflux for 1.5 hours. The reaction mixture was added portionwise into an ice-cooled 1N aqueous NaOH and extracted three times with ethyl acetate and the extracts were dried over MgSO4. The solvent was evaporated, and the residue was purified by silica gel chromatography (hexane/ethyl acetate=5/1 to 2/1) to give the title compound (0.24 g, 65%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1.5 hours
  3. extractionextracted three times with ethyl acetate
  4. dry with materialthe extracts were dried over MgSO4
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel chromatography (hexane/ethyl acetate=5/1 to 2/1)

Sources & evidence

ORD record
ord-1d1c2475e3674de8ab64011d87a8e7d4
Source dataset
uspto-grants-2005_08
Patent number
US06936736B2

Reaction notes

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