Hydrogen Peroxide → HCID 178428734, compound

HRID 2188904Notes

Reaction equation

HRID 2188904 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[CH:3]=1.[OH:15]O>CC(O)=O>[CH3:1][C:2]1[CH:7]=[CH:6][N+:5]([O-:15])=[C:4]([NH:8][C:9](=[O:14])[C:10]([CH3:11])([CH3:13])[CH3:12])[CH:3]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 35314852,2-Dimethyl-N-(4-Methyl-2-pyridyl)propionamide

Product 1

HCID 178428734HCID 178428734, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of N-(4-methylpyridin-2-yl)pivalamide (10 g, 52 mmol) in AcOH (300 ml) was added H2O2 (7.0 ml, 68 mmol) dropwise at 0° C. The mixture was stirred overnight at 70° C. The reaction mixture was quenched with water, extracted with ethyl acetate (200 mL×3) and washed with saturated Na2SO3 solution. The combined organic extracts were dried over anhydrous Na2SO4 and evaporated under vacuum. The residue was purified by chromatography on silica gel (5% ethyl acetate in petroleum ether) to afford 4-methyl-2-pivalamidopyridine 1-oxide (8.4 g, 77%). 1H NMR (CDCl3, 300 MHz) δ 10.38 (br s, 1H), 10.21 (br s, 1H), 8.34 (s, 1H), 8.26 (d, J=6.9 Hz, 1H), 6.83 (d, J=6.9 Hz, 1H), 2.37 (s, 3H), 1.33 (s, 9H).

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate (200 mL×3)
  3. washwashed with saturated Na2SO3 solution
  4. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  5. customevaporated under vacuum
  6. customThe residue was purified by chromatography on silica gel (5% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-313d158cf89a4665bdda6ea8bf698396
Source dataset
uspto-grants-2012_12
Patent number
US08324207B2

Reaction notes

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