4,4'-Dimethyl-2,2'-bipyridine → 4,4'-Dimethyl-2,2'-bipyridyl 1-Oxide

HRID 499462

Reaction equation

HRID 499462 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][N:9]=2)[CH:3]=1.ClC1C=CC=C(C(OO)=[O:23])C=1>C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][N:9]=2)[N+:5]([O-:23])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 143384,4'-Dimethyl-2,2'-bipyridineHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 135867924,4'-Dimethyl-2,2'-bipyridyl 1-OxideYield 71.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4,4′-Dimethyl-2,2′-bipyridyl (4.8 g, 26 mmol) and 3-chloroperbenzoic acid (77%, 8.7 g, 39 mmol) were dissolved in chloroform (25 ml), and the mixture was stirred at room temperature for 24 hrs. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with ethyl acetate-methanol (4:1, v/v) were collected, concentrated and crystallized from dimethyl ether to give the titled compound (3.7 g, 71%).

Workup

  1. customThe solvent was evaporated
  2. washThe fractions eluted with ethyl acetate-methanol (4:1
  3. customv/v) were collected
  4. concentrationconcentrated
  5. customcrystallized from dimethyl ether

Sources & evidence

ORD record
ord-471362b48e3a4e15af09a9129e23b9d0
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Linked notes

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