Hydrochloric Acid → O-Ethylacetanilide

Participants

Reaction Steps

To the stirred solution of commercially available ethyl aniline (16, 20.3 g, 167.5 mmol, 1 eq.) in anhydrous pyridine (90 mL), at zero degree, under argon was added acetic anhydride (32 mL, 335.04 mmol, 2 eq). After the addition, the resulting solution was stirred with warming to room temperature overnight. The reaction solution was cooled (0° C.), pH adjusted between 4 and 5 with 10% HCl, and extracted with ethyl acetate (2×500 mL). The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated to provide the title compound as a white solid.

Provenance & Evidence