Methyl iodide → 4-Pyridinecarbaldehyde oxime

HRID 2232093Notes

Reaction equation

HRID 2232093 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][C:5]([CH:8]=[N:9][OH:10])=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].IC.C(#N)C>O>[N:2]1[CH:7]=[CH:6][C:5]([CH:8]=[N:9][OH:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 137192606HCID 137192606, compound

Product 1

HCID 127644-Pyridinecarbaldehyde oximeYield 190.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4-pyridinecarboxaldehyde oxime, hydrochloride (24.5 g, 154 mmol) in 250 ml of water was treated with solid sodium bicarbonate (13 g, 155 mmol) and the resulting oil was extracted into 1.2 l of ethyl acetate. The extract was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and calcium sulfate, and concentrated to 500 ml of solution in vacuo. This concentrate was treated with iodomethane (21.5 ml, 344 mmol) and heated with 100 ml of acetonitrile under reflux for two hours. The resulting yellow salt which separated was collected by filtration and dried to provide 35.8 g of 4-pyridinecarboxaldehyde oxime, methiodide, mp 180°-182° C.

Workup

  1. extractionthe resulting oil was extracted into 1.2 l of ethyl acetate
  2. washThe extract was washed with saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate and calcium sulfate
  4. concentrationconcentrated to 500 ml of solution in vacuo
  5. temperatureunder reflux for two hours
  6. customThe resulting yellow salt which separated
  7. filtrationwas collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-34d7b735bb674d37b08411cc841ec4ad
Source dataset
uspto-grants-1988_11
Patent number
US04786648

Reaction notes

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