Hydrogen Peroxide → HCID 178436613, compound

HRID 869875Notes

Reaction equation

HRID 869875 reaction equation
[OH:1]O.[CH2:3]([C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])=[N:9][CH:10]=1)[CH3:4].O>C(O)(=O)C>[CH2:3]([C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])=[N+:9]([O-:1])[CH:10]=1)[CH3:4]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 962WaterHCID 59272530N-(5-ethylpyridin-2-yl)pivalamide

Product 1

HCID 178436613HCID 178436613, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

H2O2 (30%, 34 mL, 0.33 mol) was added to a solution of N-(5-ethylpyridin-2-yl)pivalamide (22 g, 0.11 mol) in acetic acid (200 mL). The mixture was stirred overnight at 80° C. The reaction mixture was poured into water and was extracted with EtOAc. The organics were washed with saturated Na2SO3 solution and NaHCO3 solution before being dried over MgSO4. The solvent was evaporated in vacuo to afford 5-ethyl-2-pivalamidopyridine 1-oxide (16 g, 67%), which was used for the next step without further purification.

Workup

  1. extractionwas extracted with EtOAc
  2. washThe organics were washed with saturated Na2SO3 solution and NaHCO3 solution
  3. dry with materialbefore being dried over MgSO4
  4. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-7a2f74b86a3f4fd2a9a48c535f43d2a1
Source dataset
uspto-grants-2015_03
Patent number
US08969386B2

Reaction notes

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