Phosphorus oxychloride → 1-(2-Chloro-1H-indol-3-yl)ethan-1-one

Participants

Reaction Steps

13.7 ml POCl3 was slowly added to a mixture of dimethylacetamide (5.6 ml) in 25 ml of chloroform, at 5° C. A solution of 6.66 g of oxindole in 25 ml chloroform was slowly added, and the reaction refluxed for 7 hours, and left overnight at room temperature with stirring. The reaction mixture was added to 250 ml of ice/water, the phases separated, and the organic phase extracted with water (4×50 ml). The aqueous phases were pooled and neutralized with sodium acetate, and stirred for 4 hours at room temperature. Filtration and drying gave (75). Yield 4.8 g.

Provenance & Evidence