Peracetic Acid → 4,4'-Dimethyl-2,2'-bipyridyl 1-Oxide

HRID 2295399Notes

Reaction equation

HRID 2295399 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.C(OO)(=[O:17])C>ClCCl.C(OCC)(=O)C>[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-:17])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 6585Peracetic AcidHCID 143384,4'-Dimethyl-2,2'-bipyridine

Product 1

HCID 135867924,4'-Dimethyl-2,2'-bipyridyl 1-Oxide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
23 °C

Procedure

27.6 g (0.15 mol) of 4,4'-dimethyl-2,2'-bipyridine are dissolved in 300 ml of dichloromethane. 86 ml of a 1.837-molar solution of peracetic acid in ethyl acetate are added dropwise at 23°-28° C. After stirring for 50 hours at 23° C., the mixture is concentrated in vacuo. 27.2 g (90% of theory) of 4.4'-dimethyl-2,2'-bipyridine 1-oxide crystallise from ethylbenzene/petroleum ether; melting point 80°-130° C. (over a range).

Workup

  1. concentrationthe mixture is concentrated in vacuo
  2. custom27.2 g (90% of theory) of 4.4'-dimethyl-2,2'-bipyridine 1-oxide crystallise from ethylbenzene/petroleum ether

Sources & evidence

ORD record
ord-56bc2bd8fefa4cdaa3160f93b0e02475
Source dataset
uspto-grants-1984_01
Patent number
US04424359

Reaction notes

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