Hydrochloric Acid → N-Hydroxy-N-methyl-3-(4-methylphenyl)prop-2-enamide

Participants

Reaction Conditions

Reaction Steps

A solution of 4-methylcinnamic acid (1.62 g, 10 mmol) and oxalyl chloride (2.0 ml, 23 mmol) in 50 ml anhydrous tetrahydrofuran (THF) was stirred at reflux for two hours, then concentrated in vacuo. The residue was redissolved in 30 ml THF, and added dropwise to a solution of N-methyl-hydroxylamine hydrochloride (1.26 g, 15 mmol) and triethylamine (5.0 ml, 36 mmol) in 50 ml of 2:1 THF-water at 0° C. The mixture was stirred for one hour at 0° C., then for one hour at room temperature, and then poured into excess 5% aqueous hydrochloric acid. The resulting mixture was extracted with ethyl ether, and the ether extract washed successively with 5% aqueous hydrochloric acid and brine, dried over sodium sulfate, and evaporated. Recrystallization of the residue from ethyl acetate provided 1.48 g (77% yield) of the titled compound, mp 142°-144° C.

Provenance & Evidence