2,2'-Bipyridine → 6,6'-Dimethyl-2,2'-bipyridine-N-oxide

HRID 1586925Notes

Reaction equation

HRID 1586925 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[N:9]=2)[CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:23])C=1.C1C=CN=C(C2C=CC=CN=2)C=1>C(Cl)(Cl)Cl>[CH3:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=2)[N+:9]=1[O-:23]

Participants

5

Reactant 3

HCID 14742,2'-BipyridineHCID 204456,6'-Bi-2-picolineHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 109980306,6'-Dimethyl-2,2'-bipyridine-N-oxide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

6,6'-Dimethyl-2,2'-bipyridine (1.97 g, 0.0107 moles, Example 1) was dissolved in chloroform (10 ml). m-Chloroperbenzoic acid (1.85 g, 0.0107 moles) was dissolved in chloroform (40 ml), and added slowly to the bipyridine solution at 0°-5° C. After stirring for two hours at room temperature the solution was extracted twice with saturated sodium hydrogen carbonate solution and three times with water. The chloroform phase was dried and evaporated. The product was purified by flash chromatography.

Workup

  1. extractionwas extracted twice with saturated sodium hydrogen carbonate solution and three times with water
  2. dry with materialThe chloroform phase was dried
  3. customevaporated
  4. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-3bc634c8fe4247f2b15af7a3d9d97440
Source dataset
uspto-grants-1993_06
Patent number
US05216134

Reaction notes

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