Hydrogen Peroxide → 5-Bromo-N,N-dimethylpyridine-2-carboxamide 1-oxide

HRID 1177272Notes

Reaction equation

HRID 1177272 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:10]([CH3:12])[CH3:11])=[O:9])=[N:6][CH:7]=1.[OH:13]O>CC(O)=O>[Br:1][C:2]1[CH:7]=[N+:6]([O-:13])[C:5]([C:8]([N:10]([CH3:12])[CH3:11])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 228316185-bromo-N,N-dimethylpicolinamide

Product 1

HCID 595600395-Bromo-N,N-dimethylpyridine-2-carboxamide 1-oxideYield 98%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
78 °C

Procedure

To a solution of 5-bromo-N,N-dimethylpyridine-2-carboxamide (730 mg, 3.19 mmol) in 10 mL of HOAc was added 1 ml of 35% H2O2. After stirring the mixture at 78° C. for 14 hours, it was cooled and concentrated under reduced pressure. The residue was made alkaline with excess solid Na2CO3 and diluted with 25 mL of CHCl3 with stirring. The inorganic salts were filtered off, and the organic layer was dried over Na2SO4. The solvent was evaporated under reduced pressure to provided the product (750 mg, 98%), which was used without further purification. MS (ESI, pos): 247.00.

Workup

  1. temperatureit was cooled
  2. concentrationconcentrated under reduced pressure
  3. additiondiluted with 25 mL of CHCl3
  4. stirringwith stirring
  5. filtrationThe inorganic salts were filtered off
  6. dry with materialthe organic layer was dried over Na2SO4
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-660e406e1ef64827b942e124b0d48d5d
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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