Ammonium Chloride → HCID 20328821, compound

Participants

Reaction Conditions

Reaction Steps

Several drops of ethyl bromide were added to a stirred suspension of 1.29 g. (0.054 g.-atom) of magnesium turnings in 5 ml. of tetrahydrofuran under a nitrogen atmosphere. After the reaction began 9.3 g. (0.054 mole) of 3-chloroquinolizidine in 100 ml. of tetrahydrofuran was added. After the addition was completed the mixture was stirred and refluxed for one hour and cooled to 0° C. To the chilled suspension of the Grignard reagent was added a solution of 12.55 g. (0.051 mole) of 2-chloro-9-thioxanthone in 300 ml. of tetrahydrofuran. The solution was stirred at 24° C. for two hours, poured into aqueous ammonium chloride and extracted with ether. The extracts were washed with water, dried and evaporated to give 2-chloro-9-(3-quinolizidinyl)-9-hydroxythioxanthene.

Provenance & Evidence