O-Methylhydroxylamine hydrochloride → 2-(2-hydroxymethylphenyl)-2-methoxyimino-N-methylacetamide

Methoxyamine hydrochloride (0.22 g, 0.0026 mol) was dissolved in methanol (2 ml), and a 28% sodium methoxide-methanol solution (0.58 g, 0.003 mol) was added to the solution to obtain a suspension. A mixed solution of 2-[2-{(1-ethoxyethyl)oxymethyl}phenyl)-N-methyl-2-oxoacetamide (0.53 g, 0.002 mol) and methanol (2 ml) was added to the suspension. The mixture was stirred under ref lux for 3 hours, and then cooled to room temperature. After cooling, p-toluenesulfonic acid monohydrate (0.19 g, 0.001 mol) was added, and the mixture was stirred at room temperature for 1 hour. 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 (0.37 g, Yield: 83.2%, E/Z=97/3) as colorless crystals.

1. customto obtain a suspension
2. temperatureAfter cooling
3. stirringthe mixture was stirred at room temperature for 1 hour
4. additionwas added
5. extractionthe mixture was extracted with dichloromethane (50 ml) twice
6. dry with materialThe extract was dried over anhydrous magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

ORD record

ord-9b53188d0ec54a4aae042bfec2f1ff17

Source dataset

uspto-grants-2000_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06147231