Carbon Dioxide → 2-Phenyl-6-quinolineacetic acid

Participants

Reaction Steps

The Grignard compound is prepared in the customary manner from 5 g of 6-bromomethyl-2-phenyl-quinoline and magnesium in 30 ml of diethyl ether. It is added to a solution of solid carbon dioxide in 100 ml of diethyl ether. At the same time a further quantity of solid carbon dioxide is added in portions to the reaction solution. Thereafter, aqueous ammonium chloride solution is added to the reaction mixture and the whole is extracted with ethyl acetate. The organic phases are extracted with 2 N sodium carbonate solution. The sodium carbonate extracts are adjusted to pH 6 and extracted with ethyl acetate. These ethyl acetate layers are dried and evaporated. The residue, after recrystallisation from methanol-pentane, yields 2-phenyl-6-quinolineacetic acid of melting point 176-179°C.

Provenance & Evidence