Water → HCID 54428942, compound

HRID 1739658Notes

Reaction equation

HRID 1739658 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].[Br:19][C:20]1[CH:21]=[C:22]([CH3:27])[C:23](F)=[N:24][CH:25]=1.O>C1COCC1>[CH3:18][O:17][N:16]=[C:11]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[CH2:4][O:3][C:23]1[C:22]([CH3:27])=[CH:21][C:20]([Br:19])=[CH:25][N:24]=1)[C:12]([NH:14][CH3:15])=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 120569025-Bromo-2-fluoro-3-methylpyridineHCID 544725602-(2-hydroxymethylphenyl)-2-methoxyimino-N-methylacetamide

Product 1

HCID 54428942HCID 54428942, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

Sodium hydride (60%, 0.18 g, 4,5 mmol) was added to a solution of 2-hydroxymethyl-α-methyoxyimino-N-methyl-benzeneacetamide (1.0 g, 4.5 mmol) in dry THF (25 mL) and stirred for 10 minutes at 25° C. under N2 atmosphere. The pyridine product of Example 1 (0.86 g, 4.5 mmol) was added to this reaction mixture and stirred for 16 hours. Water (20 mL) was added and the resulting mixture was extracted with ether (3×50 mL), dried (anhydrous Na2SO4), filtered and concentrated in vacuo to yield crude residue (1.5 g), which was then triturated with ether/pentane to give α-(methoxyimino)-N-methyl-2-[[[5-bromo-3-methyl-2-pyridinyl]oxy]methyl]-benzeneacetamide (1.1 g) as a white solid. M.P. 115-116° C.

Workup

  1. stirringstirred for 16 hours
  2. extractionthe resulting mixture was extracted with ether (3×50 mL)
  3. dry with materialdried (anhydrous Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto yield crude residue (1.5 g), which
  7. customwas then triturated with ether/pentane

Sources & evidence

ORD record
ord-6f158ceb4b5b4723965e68f63ad13104
Source dataset
uspto-grants-1999_10
Patent number
US05968875

Reaction notes

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