4-Iodoquinoline

Chemical Properties

Blue-green solid

Uses

4-Iodoquinoline is a reagent used in the synthesis of aryl hydantoin Ro 13-3978 a antischistosomal compound that produces antiandrogenic side effects.

Synthesis

A solution of 4-chloroquinoline (5.0 g, 30.56 mmol) in was treated with sodium iodide (23 g, 153 mmol) and 47% hydriodic acid (20 mL) at room temperature. 2-butanone (40 mL) in , refluxed with heat for 8 h, cooled to room temperature, adjusted to pH with saturated NaHCO3 7 and extracted with ethyl acetate. The extract was concentrated and the concentrate was purified by silica gel fast column chromatography using 4:1/hexane:ethyl acetate to give the desired product 4-iodoquinoline.