Methyl iodide → HCID 18649180, compound

HRID 1681306Notes

Reaction equation

HRID 1681306 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=[N:17][OH:18])[CH2:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1.[H-].[Na+].[CH3:21]I>C(COC)OC>[CH3:21][O:18]/[N:17]=[C:9](/[C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[F:1])\[CH2:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86746405HCID 86746405, compound

Product 1

HCID 18649180HCID 18649180, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 2',4'-difluoro-2-(3-pyridyl)acetophenone oxime in 25 ml of dimethoxyethane is treated in portions with 0.50 g of sodium hydride dispersion (55% in oil) and the mixture is stirred at room temperature for 30 minutes. 1.8 g of methyl iodide is then added and the mixture is heated to reflux temperature. After 4 hours, it is cooled to room temperature, poured onto ice and extracted with ethyl acetate, and the organic phase is dried over anhydrous magnesium sulfate and concentrated under reduced pressure. After separation by column chromatography on silica gel, (E)-2',4'-difluoro-2-(3-pyridyl)acetophenone O-methyloxime [1H-NMR (CDCl3, 200 MHz): 4.05 ppm (s, CH3O--N=)] is obtained first and then (Z)-2',4'-difluoro-2-(3-pyridyl)acetophenone O-methyloxime [1H-NMR (CDCl3, 200 MHz): 3.91 ppm (s, CH3O--N=)].

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux temperature
  3. waitAfter 4 hours
  4. temperatureit is cooled to room temperature
  5. additionpoured onto ice
  6. extractionextracted with ethyl acetate
  7. dry with materialthe organic phase is dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customAfter separation by column chromatography on silica gel

Sources & evidence

ORD record
ord-a7e400d6421a4dde8ac1fa919ad4d61e
Source dataset
uspto-grants-1992_12
Patent number
US05171354

Reaction notes

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