Hydrochloric Acid → Dimoxystrobin

Participants

Reaction Conditions

Reaction Steps

Methyl alcohol (10 ml) and a 50% aqueous solution (1.15 g, 6 mmol) of methoxylamine.1/2 sulfate were added to N-methyl-2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-oxo-acetamide (1.49 g, 5 mmol). The mixture was refluxed for 6 hours. After completion of the reaction, methyl alcohol was evaporated under reduced pressure. Toluene (10 ml) and conc. hydrochloric acid (1.04 g, 10 mmol) were added to the resulting residue (E/Z=47/53). The mixture was heated at 80° C. for 2 hours. After cooling, toluene (100 ml) was added to the reaction mixture. The mixture was washed with water (100 ml), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to give (E)-N-methyl-2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-methoxyiminoacetamide (1.56 g, Yield: 95.5%, E/Z=95/5).

Provenance & Evidence