m-Chloroperbenzoic acid → HCID 89649701, compound

HRID 2207649Notes

Reaction equation

HRID 2207649 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([F:18])=[C:8]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([C:16]#[N:17])[CH:11]=2)[CH:9]=1)[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:27])C=1>C(Cl)Cl.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([F:18])=[C:8]([C:10]2[CH:15]=[CH:14][N+:13]([O-:27])=[C:12]([C:16]#[N:17])[CH:11]=2)[CH:9]=1)[CH3:2]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 89649569HCID 89649569, compound

Product 1

HCID 89649701HCID 89649701, compoundYield 77.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 656671Sodium PyrosulfiteSolvent

Procedure

A solution of 4-(5-ethoxy-2-fluoro-phenyl)pyridine-2-carbonitrile (which may be prepared as described in Description 111) (6.19 g, 25.55 mmol) in DCM (200 mL) was treated with mCPBA (7.56 g, 30.66 mmol) and then was reluxed under nitrogen for 3 days. The mixture was diluted with 5% sodium metabisulfite (100 ml) and DCM (200 ml) and shaken vigourously. The organic layer was then washed with sat NaHCO3 solution (200 ml) and then dried (Na2SO4) and concentrated. Purification by flash chromatography gave 4-(5-ethoxy-2-fluoro-phenyl)-1-oxido-pyridin-1-ium-2-carbonitrile (D112) (5.102 g);

Workup

  1. washThe organic layer was then washed with sat NaHCO3 solution (200 ml)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customPurification by flash chromatography

Sources & evidence

ORD record
ord-102910ebc818476699071ed28287c5f8
Source dataset
uspto-grants-2016_06
Patent number
US09376436B2

Reaction notes

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