Methanesulfonyl chloride → 8-Chloro-5,6,7,8-tetrahydroquinoline

Participants

Reaction Conditions

Reaction Steps

At ambient temperature, 3 ml of methane sulfonyl chloride were added slowly to 1.49 g of 5,6,7,8-tetrahydroquinoline-N-oxide with stirring under an inert atmosphere. The mixture was heated for 4 hours at 80° to 82° C., then cooled to 20° C. and poured into 20 ml of a saturated solution of sodium bicarbonate. Then, sodium bicarbonate was added until an alkaline pH was obtained and after extracting with methylene chloride, washing with water, drying the re-united organic solutions and distilling to dryness under reduced pressure, 1.53 g of 8-chloro-5,6,7,8-tetrahydroquinoline was obtained in the form of an oil.

Provenance & Evidence