4,4'-Bipyridine → 4,4'-Bipyridine, 1-oxide

HRID 1245480Notes

Reaction equation

HRID 1245480 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.ClC1C=C(C=CC=1)C(OO)=[O:18]>C(Cl)Cl>[N+:1]1([O-:18])[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 111074,4'-BipyridineHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 122991544,4'-Bipyridine, 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of 4,4′-bipyridine (25.00 g, 160.08 mmol, 1 equiv) in CH2Cl2 (200 mL) at 0° C. was added 3-chloroperoxybenzoic acid (35.87 g, 77%, 160.06 mmol, 1 equiv). The reaction mixture was stirred overnight at rt. The solid was filtered off and the filtrate was concentrated and purified by flash column chromatography (acetone to 10% MeOH in acetone) to give 4,4′-bipyridine-1-oxide (3-1) as a solid. 1H NMR (CDCl3) δ 8.75 (d, 2H, J=5.9), 8.31 (d, 2H, J=7.1), 7.57 (d, 2H, J=7.0), 7.50(d, 2H, J=6.1).

Workup

  1. filtrationThe solid was filtered off
  2. concentrationthe filtrate was concentrated
  3. custompurified by flash column chromatography (acetone to 10% MeOH in acetone)

Sources & evidence

ORD record
ord-b8430c7f54844990adc07339a8c4c2e7
Source dataset
uspto-grants-2006_10
Patent number
US07125888B2

Reaction notes

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