Thionyl Chloride → 2-Nitropyridine-4-carbonyl chloride

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Reaction Steps

1.8 g. of 2-nitroisonicotinic acid and 30 ml. of thionyl chloride were refluxed for 3 hours. An excess of thionyl chloride was distilled off to leave 2-nitroisonicotinoyl chloride as an oil. The obtained acid chloride was added to 5 ml. of pyridine at -15° C., and to the resulting solution was added 1.5 g. of m-toluylamide. The mixture was stirred at room temperature for one hour and the solvent was evaporated at 40° C under reduced pressure. The residue was then purified by silica gel chromatography and recrystallized from ethyl acetate-n-hexane to yield 250 mg. of the desired crystals.

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