O-Methylhydroxylamine hydrochloride → 2-[2-{(1-ethoxyethyl)oxymethyl}phenyl]-2-methoxyimino-N-methylacetamide

HRID 1857816Notes

Reaction equation

HRID 1857816 reaction equation
Cl.[CH3:2][O:3][NH2:4].C[O-].[Na+].CO.[CH2:10]([O:12][CH:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23](=O)[C:24]([NH:26][CH3:27])=[O:25])[CH3:14])[CH3:11]>CO.[Cl-].[Na+].O>[CH2:10]([O:12][CH:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23](=[N:4][O:3][CH3:2])[C:24]([NH:26][CH3:27])=[O:25])[CH3:14])[CH3:11]

Participants

6

Reactant 3

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 154837862-[2-{(1-ethoxyethyl)oxymethyl}phenyl)-N-methyl-2-oxoacetamideHCID 23694274Sodium methanolate methanol

Product 1

HCID 536744052-[2-{(1-ethoxyethyl)oxymethyl}phenyl]-2-methoxyimino-N-methylacetamideYield 92.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

Methoxyamine hydrochloride (0.50 g, 0.006 mol) was dissolved in methanol (6 ml), and a 28% sodium methoxide-methanol solution (1.45 g, 0.0075 mol) was added to the solution to obtain a suspension. A mixed solution of 2-[2-{(1-ethoxyethyl)oxymethyl}phenyl]-N-methyl-2-oxoacetamide (0.80 g, 0.003 mol) and methanol (3 ml) was added to the suspension, and the mixture was stirred under reflux for 1 hour. After completion of the reaction, half-saturated brine (150 ml) was added, and the mixture was extracted with dichloromethane (100 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 an E/Z mixture of 2-[2-{(1-ethoxyethyl)oxymethyl}phenyl]-2-methoxyimino-N-methylacetamide (0.82 g, Yield: 92.8%) as a colorless oil.

Workup

  1. customto obtain a suspension
  2. temperatureunder reflux for 1 hour
  3. additionwas added
  4. extractionthe mixture was extracted with dichloromethane (100 ml) twice
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane)
  8. customto obtain

Sources & evidence

ORD record
ord-c07e9015358b462a9aecc5dbd76d93cf
Source dataset
uspto-grants-2000_11
Patent number
US06147231

Reaction notes

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