m-Chloroperbenzoic acid → 2,3-Diphenylpyridin-1-oxide

HRID 1271239Notes

Reaction equation

HRID 1271239 reaction equation
[C:1]1([C:7]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:11][CH:10]=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=C(C=CC=1)C(OO)=[O:24]>C(Cl)(Cl)Cl>[C:1]1([C:7]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:11][CH:10]=[CH:9][N+:8]=2[O-:24])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 1184762,3-Diphenylpyridine

Product 1

HCID 229319562,3-Diphenylpyridin-1-oxideYield 86.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1 g of 2,3-diphenylpyridine was dissolved in chloroform and 1.4 g of 70% m-chloroperoxybenzoic acid was added, followed by stirring at room temperature for 15 hours. After the reaction solution was washed with an aqueous 5% potassium carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure to obtain 1.3 g of a crude crystal. The crude crystal was washed with diisopropyl ether to obtain 922 mg of the desired compound as a colorless crystal having a melting point of 167 to 170° C.

Workup

  1. washAfter the reaction solution was washed with an aqueous 5% potassium carbonate solution and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customto obtain 1.3 g of a crude crystal
  5. washThe crude crystal was washed with diisopropyl ether

Sources & evidence

ORD record
ord-d135e52eee8c49919f4b1917bc661974
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Reaction notes

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