2-Chloro-4,6-dimethyl-3-pyridinecarbonitrile → 4,6-Dimethyl-2-phenoxy-nicotinonitrile

HRID 1818896Notes

Reaction equation

HRID 1818896 reaction equation
[CH3:1][C:2]1[C:7]([C:8]#[N:9])=[C:6](Cl)[N:5]=[C:4]([CH3:11])[CH:3]=1.O.O.O.[O-:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Na+]>C1COCC1>[CH3:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:5]=[C:4]([CH3:11])[CH:3]=1

Participants

4

Reactant 2

HCID 2232612-Chloro-4,6-dimethyl-3-pyridinecarbonitrileHCID 23681143Sodium Phenoxide Trihydrate

Product 1

HCID 9469834,6-Dimethyl-2-phenoxy-nicotinonitrileYield 90.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

4,6-dimethyl-2-chloro-nicotinonitrile (600 mg, 3.60 mmol) was dissolved in 30 mL of anhydrous THF and then added with sodium phenoxide trihydrate (3.06 g, 18.00 mmol) and stirred at 80° C. overnight. The mixture was extracted with methylene chloride, dried with anhydrous sodium sulfate, filtered and then concentrated under reduced pressure. A silica gel column chromatography (10% EtOAc/Hexane) was performed on the resulting residue and 730 mg (90%) of 4,6-dimethyl-2-phenoxy-nicotinonitrile was obtained in white solid.

Workup

  1. extractionThe mixture was extracted with methylene chloride
  2. dry with materialdried with anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ee898bc2551d44c58ab3dfa0dbd5e83b
Source dataset
uspto-grants-2009_10
Patent number
US07601736B2

Reaction notes

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