m-Chloroperbenzoic acid → 3-cyclohexyl-2-methylpyridine N-oxide

HRID 250977Notes

Reaction equation

HRID 250977 reaction equation
[CH:1]1([C:7]2[C:8]([CH3:13])=[N:9][CH:10]=[CH:11][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1C=C(Cl)C=C(C(OO)=[O:22])C=1>C(Cl)Cl>[CH:1]1([C:7]2[C:8]([CH3:13])=[N+:9]([O-:22])[CH:10]=[CH:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 45098222HCID 45098222, compound

Product 1

HCID 672726033-cyclohexyl-2-methylpyridine N-oxideYield 112.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-cyclohexyl-2-methylpyridine (170 mg, 1.0 mmol), in CH2Cl2 (5 mL) was treated with MCPBA (0.33 g, 1.9 mmol) for 18 hours. The solution was then washed with saturated NaHCO3 solution (5 mL), the phases separated, and the aqueous extracted with CH2Cl2 (2×10 mL). The combined organic phases were then dried (Na2SO4), filtered, and concentrated to afford crude 3-cyclohexyl-2-methylpyridine N-oxide as a white solid (0.215 g) which was used immediately in the next reaction.

Workup

  1. washThe solution was then washed with saturated NaHCO3 solution (5 mL)
  2. customthe phases separated
  3. extractionthe aqueous extracted with CH2Cl2 (2×10 mL)
  4. dry with materialThe combined organic phases were then dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-311cde94ceb6458e91b8fa5f06145490
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

Loading…