Water → 1-[4-(5-Chloro-1H-indol-3-yl)pyridin-1(4H)-yl]ethan-1-one

Participants

Reaction Steps

27 ml of redistilled pyridine were added at an interior temperature of 8° to 15° C. to a mixture of 11.2 ml of acetyl chloride and 120 ml of dioxane cooled in an ice bath and a mixture of 22 g of 5-chloro-1H-indole in 120 ml of dioxane was added to the resulting suspension at 10° to 15° C. The mixture was stirred in the dark at room temperature for 7 hours and the suspension was poured into 500 ml of water. The mixture was stirred for 5 minutes and another 500 ml of water were added. The mixture was filtered and the recovered solid was empasted with 40 ml of acetonitrile, was filtered, rinsed with acetonitrile and once with ether to obtain 13.5 g of 3-(1-acetyl-1,4-dihydro-4-pyridyl)-5-chloro-1H-indole in the form of a pale yellow solid melting at 202° C.

Provenance & Evidence