Hydrogen Peroxide → 5-Phenyl-2-picoline N-oxide

HRID 1590091Notes

Reaction equation

HRID 1590091 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([CH3:13])=[N:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.OO.CC[O:18]CC.CCOC(C)=O>CC(O)=O.[Pd]>[C:1]1([C:7]2[CH:12]=[N+:11]([O-:18])[C:10]([CH3:13])=[CH:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 767442-Methyl-5-phenylpyridineHCID 21584169Diethylether ethylacetate

Product 1

HCID 149805285-Phenyl-2-picoline N-oxide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 100 g 5-phenyl-2-picoline in 170 mL of glacial HOAc was added 30% H2O2 and the resulting solution was heated at 70° C. overnight. After the reaction mixture was cooled to room temperature, 1 g of 10% Pd/C was added to destroy excess of H2O2. The reaction mixture was then filtered on celite, washed with toluene and the filtrate was evaporated to dryness affording a yellow solid residue. The crude material was swished with a mixture of Et2O/EtOAc (10:1) and filtered to afford the pure title product as a white solid, m.p.: 91° C.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. customto destroy excess of H2O2
  3. filtrationThe reaction mixture was then filtered on celite
  4. washwashed with toluene
  5. customthe filtrate was evaporated to dryness
  6. customaffording a yellow solid residue
  7. filtrationfiltered

Sources & evidence

ORD record
ord-9827f9b91e97460ca096e72a8cc2164b
Source dataset
uspto-grants-1993_04
Patent number
US05202321

Reaction notes

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