Hydrochloric Acid → 2-(9-Ethyl-9H-carbazole-3-carbonyl)benzoic acid

Participants

Reaction Steps

To a mixture of 8.17 g (0.05 mole) of N-ethylcarbazole and 3.7 g (0.025 mole) of phthalic anhydride in 112 g of chlorobenzene, 6.65 g (0.05 mole) of aluminum chloride was added in small increments at ambient temperature after which the mixture was warmed in the range of 50°-70° C. for two hours. The reaction mixture was poured onto ice and rendered acidic by the addition of 10 percent hydrochloric acid. The chlorobenzene layer was separated and steam:distilled to remove the chlorobenzene. The residue was extracted with 10 percent agueous sodium hydroxide, filtered to remove the insolubles and then acidified with dilute hydrochloric acid. The solid which separated was collected by filtration, washed with water and dried to obtain 2-[(9-ethyl-3-carbazolyl)carbonyl]benzoic acid (Formula VII: R°=R1 =R2 =R3 =H; R8 =CH2CH3) melting over the range 120°-130° C.

Provenance & Evidence