2-Chloro-N-(4-methoxyphenyl)acetamide → 5-Hydroxyoxindole

Participants

Reaction Conditions

Reaction Steps

2-chloro-N-(4-methoxyphenyl)-acetamide (10 g) and Anhydrous aluminum trichloride (17 g) was heated to 120° C. for 15 minutes and then heated to 240° C. for 1 hour. The reaction was cooled to room temperature and quenched with ice water and Concentrate hydrochloride acid, and extracted with ethyl acetate (5×). Organic layers combined and dried over magnesium sulfate, filtered and concentrated in vacuo. The crude solid was flash chromatography (silica, ethyl acetate) to give product.

Provenance & Evidence