Ammonia → Methyl N-hydroxy-2-phenylethanimidate

Participants

Reaction Steps

Methyl phenylacetimidate hydrochloride (30.9 grams; 0.167 mole) was stirred with solid hydroxylamine hydrochloride (12.8 grams; 0.184 mole) in dimethyl formamide (120 ml) while ammonia gas was added slowly without cooling. Ammonia addition (approximately 5 grams) was stopped when the temperature of the mixture peaked at 40° C. and dropped to 29° C. The slurry was then cooled in an ice bath and filtered. The filtrate (131 grams) was analyzed by GC and GC-mass spectroscopy and established to contain methyl N-hydroxyphenylacetimidate (23.4 grams; 84.8% yield).

Provenance & Evidence