m-Chloroperbenzoic acid → HCID 18377464, compound

HRID 1255902Notes

Reaction equation

HRID 1255902 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[CH:4][N:3]=1.C1C=C(Cl)C=C(C(OO)=[O:20])C=1.S(=O)(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[CH:4][N+:3]=1[O-:20]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516919Sodium BisulfateHCID 573459814-tert-Butyl-2-chloropyridine

Product 1

HCID 18377464HCID 18377464, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-Chloro-4-t-butylpyridine (5.0 g, 30 mmol) was dissolved in chloroform (75 mL), treated with MCPBA, ca. 75% (8.3 g, 36 mmol, 1.2 equivalents) and heated to reflux for 19 h. The mixture was stirred with sodium bisulfate solution until testing with starch-iodide paper indicated consumption of oxidant. The pH was adjusted to 7 with saturated aqueous NaHCO3 solution, the phases separated and the aqueous phase extracted once with CH2Cl2. The organic phases were pooled and washed twice with H2O, once with brine, dried (Na2SO4) and concentrated in vacuo to afford 2-chloro-4-t-butylpyridine-N-oxide (5.0 g, 90%), which crystallized to long white needles on standing.

Workup

  1. temperatureheated
  2. temperatureto reflux for 19 h
  3. customconsumption of oxidant
  4. customthe phases separated
  5. extractionthe aqueous phase extracted once with CH2Cl2
  6. washwashed twice with H2O, once with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dcfbd2ad85bd4338b4ffda44114106da
Source dataset
uspto-grants-2013_06
Patent number
US08461164B2

Reaction notes

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