Water → 2-[[[6-fluoro-2-pyridinyl]oxy]methyl]-alpha-(methoxyimino)-N-methyl-benzeneacetamide

HRID 2303429Notes

Reaction equation

HRID 2303429 reaction equation
[H-].[Na+].[OH:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11](=[N:16][O:17][CH3:18])[C:12]([NH:14][CH3:15])=[O:13].[F:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22](F)[N:21]=1.O>C1COCC1>[F:19][C:20]1[N:21]=[C:22]([O:3][CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:11](=[N:16][O:17][CH3:18])[C:12]([NH:14][CH3:15])=[O:13])[CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 739342,6-DifluoropyridineHCID 544725602-(2-hydroxymethylphenyl)-2-methoxyimino-N-methylacetamide

Product 1

HCID 599085732-[[[6-fluoro-2-pyridinyl]oxy]methyl]-alpha-(methoxyimino)-N-methyl-benzeneacetamideYield 78.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaH (7.0 g, 60% oil dispersion, 0.176 mol) was added portionwise over five minutes to a stirred slurry of 2-(hydroxymethyl)-α-(methoxyimino)-N-methyl-benzeneacetamide (35.8 g, 0.161 mol) in 700 mL THF. After the resulting mixture was stirred for 3.25 hours, 2,6-difluoropyridine (15.4 g, 0.134 mol) was added neat over a 20 minute period, and the mixture was stirred overnight at room temperature. Water (250 mL) was added, THF was removed in vacuo, and the aqueous residue was extracted three times with 250 mL CH2Cl2. The combined extracts were washed with brine (250 mL), filtered through Na2SO4, and concentrated in vacuo. The residue was purified by silica gel chromatography (5% CH3CN in CH2Cl2) to yield 2-[[[6-fluoro-2-pyridinyl]oxy]methyl]-α-(methoxyimino)-N-methyl-benzeneacetamide (33.2 g, 78%).

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. customTHF was removed in vacuo
  3. extractionthe aqueous residue was extracted three times with 250 mL CH2Cl2
  4. washThe combined extracts were washed with brine (250 mL)
  5. filtrationfiltered through Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel chromatography (5% CH3CN in CH2Cl2)

Sources & evidence

ORD record
ord-31960a728a7247cdb269ec06a08cffa0
Source dataset
uspto-grants-2002_08
Patent number
US06432990B1

Reaction notes

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