Archives for Chemistry Experiments of 4,5-Dichloro-3(2H)-pyridazinone

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The functionalization of 4,5-dichloropyridazin-3(2H)-one and 4,5-dichloro-2-methyl-6-nitropyridazin-3(2H)-one was reported. A mixture of 4,5-dichloropyridazin-3(2H)-one, potassium nitrate and conc-sulfuric acid was stirred for 5 hours at 110-120C. After cooling to room temperature, the solution was slowly poured into ice-water. The resulting yellow crystals was filtered, washed with water and dried in air to give the product. A mixture of 4,5-dichloro-6- nitropyridazin-3(2H)-one and POCl3 was refluxed for 24 hours. After cooling to room temperature, the solution was evaporated under reduced pressure. The resulting residue was slowly poured into ice-water (300 mL). Chlorination of compound 4,5-dichloro-6- nitropyridazin-3(2H)-one with phosphorus oxychloride also gave 3,4,5-trichloro-6-nitropyridazine in 72% yield. Three proton signals were also detected at d 9.0 (1H), 8.64 (1H) and 6.20 (2H) ppm in the spectrum of 1H NMR.

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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2365 – PubChem