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Sodium Sulfite → 3,6-Dimethyl-2-pyridinecarbonitrile 1-oxide

HRID 2356631
Notes
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Reaction equation

HRID 2356631 reaction equation
[CH3:1][C:2]1[C:3]([C:9]#[N:10])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.ClC1C=CC=C(C(OO)=[O:19])C=1.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[N+:4]([O-:19])[C:3]=1[C:9]#[N:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 121756763,6-Dimethylpicolinonitrile

Product 1

HCID 684559153,6-Dimethyl-2-pyridinecarbonitrile 1-oxideYield 58%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 3,6-dimethyl-2-pyridinecarbonitrile (8.20 g, may be prepared as described in Russell et al., J. Med. Chem., 48(5), 1367, (2005)) in chloroform (60 ml) was added dropwise a solution of m-chloroperbenzoic acid (20 g) in chloroform (210 ml) and the solution stirred at ambient temperature for 7 hours. Sodium sulphite (2.4 g) was added and the mixture stirred for 1.5 hours, filtered and the solid washed with dichloromethane. The filtrate was washed with saturated sodium bicarbonate (120 ml) and water (120 ml), dried (MgSO4) and concentrated in vacuo. The residue was recrystallised from ether to afford the title compound (5.28 g, 58%) as a pale yellow solid.

Workup

  1. stirringthe mixture stirred for 1.5 hours
  2. filtrationfiltered
  3. washthe solid washed with dichloromethane
  4. washThe filtrate was washed with saturated sodium bicarbonate (120 ml) and water (120 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was recrystallised from ether

Sources & evidence

ORD record
ord-a9891d17d33b49c181bff7cf09273eb8
Source dataset
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07759369B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes