Quinoline → Ethyl 1,4 dimethyl-5-(rho-toluoyl)-pyrrole-2-acetate

Participants

Reaction Conditions

Reaction Steps

A solution of 330 g. (0.096 mole) of ethyl 3-carboxy-1,4-dimethyl-5-(ρ-toluoyl)-pyrrole-2-acetate in 200 ml. of quinoline with 0.1 gm copper chromite added is heated under nitrogen for six hours at 200° C. then for 30 mins. at 220° C. The quinoline is distilled off in vacuo. The residue is dissolved in ether and washed successively with dilute hydrochloric acid, dilute sodium hydroxide, and brine; dried over magnesium sulfate; and the solvent evaporated in vacuo to give a brown oily residue which crystallizes. It is recrystallized from methanol, sublimed at 150° C. (0.025 mm./Hg) and recrystallized from hexane to give ethyl 1,4-dimethyl-5-(ρ-toluoyl)-pyrrole-2-acetate as a white solid, M.P. 90°-93° C.

Provenance & Evidence