Sodium hydride → 1-(4,6-Dimethyl-2-pyridinyl)ethanone O-[(2-Fluoro-6-methoxyphenyl)methyl]oxime

HRID 1357025Notes

Reaction equation

HRID 1357025 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9](=[N:11][OH:12])[CH3:10])[CH:3]=1.[H-].[Na+].[F:15][C:16]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[C:17]=1[CH2:18]Cl>CN(C)C=O>[F:15][C:16]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[C:17]=1[CH2:18][O:12][N:11]=[C:9]([C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[N:5]=1)[CH3:10]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 129793072-(Chloromethyl)-1-fluoro-3-methoxybenzeneHCID 1363363511-(4,6-Dimethyl-2-pyridinyl)ethanone oxime

Product 1

HCID 854489071-(4,6-Dimethyl-2-pyridinyl)ethanone O-[(2-Fluoro-6-methoxyphenyl)methyl]oxime

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

On the other hand, 0.46 g (2.80 mmol) of 1-(4,6-dimethyl-2-pyridinyl)ethanone oxime was dissolved in 10 ml of N,N-dimethylformamide, and the resultant solution was added with 0.13 g (3.36 mmol) of sodium hydride (60%, oiliness) while cooling the solution with ice. Then, the obtained solution was stirred for 30 min. at the same temperature and subsequently added with the whole amount of the crude product of 2-fluoro-6-methoxybenzyl chloride obtained as described above while cooling the solution with ice. The resultant mixture was. further stirred for 40 min. at a room temperature, and the reacted mixture was poured into ice water and then subjected to an extraction with diethyl ether. The resultant nonaqueous layer was washed with water and the dried with anhydrous magnesium sulfate. The dried nonaqueous layer was then condensed under reduced pressure to obtain a crude product. Then, said crude product was purified by means of silica gel column chromatography (eluate; hexane:ethyl acetate=7:3 v/v) to obtain the target compound in an amount of 0.55 g. Melting point: 87-89° C.

Workup

  1. temperaturewhile cooling the solution with ice
  2. customobtained
  3. temperaturewhile cooling the solution with ice
  4. stirringfurther stirred for 40 min. at a room temperature
  5. extractionsubjected to an extraction with diethyl ether
  6. washThe resultant nonaqueous layer was washed with water
  7. dry with materialthe dried with anhydrous magnesium sulfate
  8. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-3c6d65233d6f48488d8c44890a37d5ea
Source dataset
uspto-grants-2003_07
Patent number
US06589967B1

Reaction notes

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