m-Chloroperbenzoic acid → 4-(4-isopropyl-phenyl)-pyridine-N-oxide

HRID 628833Notes

Reaction equation

HRID 628833 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].ClC1C=C(C=CC=1)C(OO)=[O:21]>ClCCl>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][N+:13]([O-:21])=[CH:14][CH:15]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 229510894-(4-Isopropylphenyl)pyridine

Product 1

HCID 692333644-(4-isopropyl-phenyl)-pyridine-N-oxideYield 78.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Part B. A solution of 4-(4-isopropyl-phenyl)-pyridine (1.01 g, 5.1 mmol) in dichloromethane (20 mL) is cooled to 0° C., and a solution of m-chloroperoxybenzoic acid (1.33 g, 7.6 mmol) in dichloromethane (20 mL) is added dropwise. The mixture is allowed to warm to ambient temperature over 12 h. with stirring, then heated to reflux for 2 h. An excess of m-chloroperoxybenzoic acid (0.5 g) is added, and reflux continued for 2 h. The solution is cooled and washed successively with 10% aq. sodium sulfite, 10% aq. sodium carbonate and saturated brine. The organic phase is dried over anhydrous magnesium sulfate and evaporated. The residue is separated by flash chromatography to afford 4-(4-isopropyl-phenyl)-pyridine-N-oxide (0.85 g, 78%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 h
  3. temperaturereflux
  4. temperatureThe solution is cooled
  5. washwashed successively with 10% aq. sodium sulfite, 10% aq. sodium carbonate and saturated brine
  6. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  7. customevaporated
  8. customThe residue is separated by flash chromatography

Sources & evidence

ORD record
ord-110aa4dd2e394564ad89aa603fd11b83
Source dataset
uspto-grants-2016_04
Patent number
US09315467B2

Reaction notes

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