Hydrochloric Acid → 2-(2-hydroxymethylphenyl)-2-methoxyimino-N-methylacetamide

HRID 1857818Notes

Reaction equation

HRID 1857818 reaction equation
CO.Cl.[CH3:4][O:5][N:6]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][O:19]C1CCCCO1)[C:8]([NH:10][CH3:11])=[O:9]>[Cl-].[Na+].O>[OH:19][CH2:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:7](=[N:6][O:5][CH3:4])[C:8]([NH:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 53869643HCID 53869643, compound

Product 1

HCID 544725602-(2-hydroxymethylphenyl)-2-methoxyimino-N-methylacetamideYield 94.6%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

Methanol (2 ml) and a 36% aqueous hydrochloric acid solution (0.01 g, 0.0001 mol) were added to an E/Z mixture of 2-methoxyimino-N-methyl-2-[2-(2-tetrahydropyranyloxymethyl)phenyl]acetamide (0.31 g, 0.001 mol), and the mixture was stirred at room temperature for 30 minutes. After completion of the reaction, half-saturated brine (80 ml) was added, and the mixture was extracted with dichloromethane (50 ml) twice. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to obtain 2-(2-hydroxymethylphenyl)-2-methoxyimino-N-methylacetamide (0.21 g, Yield: 94.6%, E/Z=97/3) as colorless crystals.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with dichloromethane (50 ml) twice
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-c185cc7c436440ff96d1c8d3080623bf
Source dataset
uspto-grants-2000_11
Patent number
US06147231

Reaction notes

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