Quinoline → HCID 178425913, compound

Participants

Reaction Conditions

Reaction Steps

A 22 liter 3-necked round bottom flask, fitted with an overhead stirrer, thermometer, and a distillation head was placed in a heating mantle and charged with quinoline (6 liter), 3-bromo-4-methylbenzoic acid (2.75 kg, 12.79 mole), thiophenol (1.75 kg 15.22 mole) and cuprous oxide (958 g, 6.7 mole). The red slurry was placed under a nitrogen blanket and heated with stirring to 180°-200° C. over a 1 hour period collecting the water as it distills. This temperature was maintained for 0.5 hours. The mixture was cooled to 110° C. and then transferred to a stirred solution of 6N hydrochloric acid. After stirring overnight, the product was collected by suction filtration, washed with 6N hydrochloric acid (19 liters) and then with water until neutral (alk-acid paper). The filter cake was washed with isopropanol and dried at 40° C. in vacuo to yield the title compound as a tan solid (2.97 kg, 95% yield, 91% purity).

Provenance & Evidence