2,2'-Bipyridine → 2,2'-Bipyridine, 1-oxide

HRID 1383052Notes

Reaction equation

HRID 1383052 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1.ClC1C=C(C=CC=1)C(OO)=[O:18]>C(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N+:8]=1[O-:18]

Participants

4

Reactant 2

HCID 14742,2'-BipyridineHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 364632,2'-Bipyridine, 1-oxideYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 25.0 grams (0.160 mole) of 2,2'-bipyridine and 33.1 grams (0.163 mole) of 85% pure m-chloroperoxybenzoic acid in 500 ml of methylene chloride was stirred at ambient temperature for 16 hours. TLC analysis of the reaction mixture indicated it to be a mixture of starting materials, the mono- and the di-oxides. One-third of the reaction mixture was placed on a column of silica gel. The column was eluted with diethyl ether to collect starting materials, and with 10% methanol-methylene chloride to collect the mono-oxide. The appropriate fractions were combined and concentrated under reduced pressure to yield 8.0 grams of 2-(2-pyridinyl)pyridine-N oxide, as an oil which solidified on standing. The remaining two-thirds of the reaction mixture was subjected to column chromatography as described above to yield an additional 13.9 grams of 2-(2-pyridinyl)pyridine-N oxide. The nmr spectra were consistent with the proposed structure.

Workup

  1. additiona mixture of starting materials
  2. washThe column was eluted with diethyl ether
  3. customto collect
  4. customwith 10% methanol-methylene chloride to collect the mono-oxide
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-560b70cf365440e082824b2f8e231afd
Source dataset
uspto-grants-1989_02
Patent number
US04808722

Reaction notes

Loading…