3,4-Dimethylpyridine → 3,4-Dimethylpyridine 1-oxide

HRID 869886Notes

Reaction equation

HRID 869886 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH3:8].C1C=C(Cl)C=C(C(OO)=[O:17])C=1>ClCCl>[CH3:1][C:2]1[CH:3]=[N+:4]([O-:17])[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 114173,4-DimethylpyridineHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 3024543,4-Dimethylpyridine 1-oxideYield 61.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3,4-dimethylpyridine (100.0 g, 0.93 mol) in dichloromethane was added m-CPBA (320.0 g, 1.87 mol) at the room temperature. The reaction mixture was stirred at room temperature overnight, and then quenched with saturated solution of Na2S2O3 (100 mL). The organic layer was separated and the aqueous phase was extracted with CH2Cl2 (300 mL×3). The combined organic layers were dried over anhydrous Na2SO4, filtered and evaporated under vacuum to yield a residue that was purified by column chromatography on silica gel (10-100% MeOH in EtOAc) to give 3,4-dimethylpyridine 1-oxide (70.0 g, 61%).

Workup

  1. customquenched with saturated solution of Na2S2O3 (100 mL)
  2. customThe organic layer was separated
  3. extractionthe aqueous phase was extracted with CH2Cl2 (300 mL×3)
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated under vacuum
  7. customto yield a residue that
  8. customwas purified by column chromatography on silica gel (10-100% MeOH in EtOAc)

Sources & evidence

ORD record
ord-2c3e9c84d5274d16aad9c3416c7d3d69
Source dataset
uspto-grants-2015_03
Patent number
US08969386B2

Reaction notes

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