Thionyl Chloride → beta-(9,10-Dihydro-9,10-methano-9-anthryl)propionic acid chloride

Participants

Reaction Steps

A solution of β-(9,10-dihydro-9,10-methano-9-anthryl)propionic acid and thionyl chloride in benzene was refluxed for 4 hours. Evaporation of excess thionyl chloride and benzene gave β-(9,10-dihydro-9,10-methano-9-anthryl)-propionic acid chloride, which was dissolved in dry tetrahydrofuran. The solution was added to a 30% aqueous monomethylamine solution at 0°-5° C. The reaction mixture was stirred at 0°-15° C., diluted with water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over anhydrous sodium sulfate and evaporated to dryness to give β-(9,10-dihydro-9,10-methano-9-anthryl)-propionic acid monomethylamide. M.P. 200°-201° C.

Provenance & Evidence