Dimethylformamide → n-[5-(2-Acetylaminoethyl)-2-methoxyphenyl]-3-oxo-butyramide

Participants

Reaction Conditions

Reaction Steps

N-[-2-(3-amino-4-methoxyphenyl)ethyl]acetamide hydrochloride (19 g) was mixed with 40 mL N,N-dimethylformamide and 18 g of diketene followed by slow addition of 3 mL of triethylamine. The mixture was stirred at 80-85° C. for 30 minutes and then poured into 300 mL of water. The aqueous solution was extracted with chloroform (2×200 mL) and the solvent was removed by rotary evaporation to yield 21.9 g (96.5%) of N-[5-(2-acetylaminoethyl)-2-methoxyphenyl]-3-oxo-butyramide as a light yellow oil. 1HNMR (DMSO-d6) spectrum was consistent with the desired product.

Provenance & Evidence