3-Cyanopyridine → Nicotinonitrile 1-oxide

HRID 233612Notes

Reaction equation

HRID 233612 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1)#[N:2].C1C=C([O:15]O)C(C(O)=O)=C(C(O)=O)C=1>C(Cl)Cl>[C:1]([C:3]1[CH:4]=[N+:5]([O-:15])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 793-CyanopyridineHCID 198097063-Hydroperoxyphthalic acid

Product 1

HCID 84686Nicotinonitrile 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 20.0 grams (0.194 mole) of 3-cyanopyridine and 142.5 grams (0.288 mole) of monoperoxyphthalic acid, magnesium salt, hexahydrate (80% pure) in 300 mL of methylene chloride is stirred at ambient temperature for about 24 hours. After this time, the mixture is filtered, and the filtrate is concentrated under reduced pressure, yielding 3-cyanopyridine N-oxide.

Workup

  1. filtrationAfter this time, the mixture is filtered
  2. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-abb8a20819494b9eb939d58ae90a4c62
Source dataset
uspto-grants-1997_01
Patent number
US05593998

Reaction notes

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