Potassium Carbonate → 4-(3-Methyl-5-cyano-2-pyridinoxy)-3,5-dichloroaniline

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Reaction Steps

To a 100 mL round bottom flask equipped with a water condenser, thermometer, magnetic stirrer, and under nitrogen atmosphere was added 2-chloro-3-methyl-5-cyanopyridine (7.10 g, 46.6 mmol), potassium carbonate (9.02 g, 65.2 mmol), 2,6-dichloro-4-aminophenol (10.77 g, 60.5 mmol), and dimethylformanide (70 mL). The resulting mixture was stirred at room temperature for 1 hour, 90° for 2 hours, and 110° for 3 hours. It was then cooled, filtered, and concentrated to give a brown mixture. This mixture was dissolved in 500 mL of toluene and washed with four 150 mL portions of 4% sodium hydroxide, water, and brine. It was then dried (Na2SO4) and concentrated to give the desired product as a brown solid (8.00 g, 27.2 mmol). m.p. 211.5°-212.5°.

Provenance & Evidence