m-Chloroperbenzoic acid → 3-Chloromethyl-2-methyl-pyridine 1-oxide

HRID 1292043Notes

Reaction equation

HRID 1292043 reaction equation
[Cl:1][CH2:2][C:3]1[C:4]([CH3:9])=[N:5][CH:6]=[CH:7][CH:8]=1.C1C=C(Cl)C=C(C(OO)=[O:18])C=1>C(Cl)(Cl)Cl>[Cl:1][CH2:2][C:3]1[C:4]([CH3:9])=[N+:5]([O-:18])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 122437113-(Chloromethyl)-2-methylpyridine

Product 1

HCID 220536063-Chloromethyl-2-methyl-pyridine 1-oxide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 3-chloromethyl-2-methylpyridine (0.50 g, 3.5 mmol) from step 2 above in CHCl3 (40 mL) was added MCPBA (1.1 g of 50% MCPBA by weight; 3.5 mmol). After 1.5 h, the solution was extracted with saturated aqueous NaHCO3 (40 mL), water (40 mL), dried (MgSO4), filtered, and evaporated under reduced pressure. The residue was purified by pressurized silica gel column chromatography using 97:3 CH2Cl2 :MeOH as eluant. 3-Chloromethyl-2-methylpyridine-N-oxide was obtained as a solid (TLC: Rf = 0.30 (97:3 CH2Cl2 :MeOH); FAB MS m/z 158 (M+ +H)).

Workup

  1. extractionthe solution was extracted with saturated aqueous NaHCO3 (40 mL), water (40 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified by pressurized silica gel column chromatography

Sources & evidence

ORD record
ord-4a7eb4576b284ad581a00e1793c2cd80
Source dataset
uspto-grants-1998_05
Patent number
US05756497

Reaction notes

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