Hydrochloric Acid → 3-Chloro-4-methyl-6-phenylpyridazine

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6.0 g (32 mmol) of 14 was placed in a 250 nit single neck round bottom flask and 30 ml acetonitrile was added to create a pale yellow slurry. 6.0 ml (64 mmol, 2 equiv) of phosphorus oxychloride was added and the reaction mixture was heated at reflux for 2.5 h. After the reaction was completed, the Mixture was cooled to ambient temperature and placed in an ice water bath. Ice water (150 mL) was slowly poured into the reaction mixture with stirring to decompose the phosphorus oxychloride into HCl and H3PO4. The solid was then collected by filtration and washed with Milli-Q water (3×50 mL). The solid was suspended in 100 mL of water and 1N NaOH was added until the aqueous suspension was at pH=8. The mixture was stirred for 5 minutes to remove all trace starting material contaminants. The solid was filtered and washed with Milli-Q water (3×100 mL). The product was dried over a medium frit sintered glass funnel in vacuo to provide 15 as a light pink powder in 96% yield. 1H NMR (DMSO-d6): δ 829 (s, 1H), 8.10 (at, 2H), 7.53 (m, 3H), 2.41 (s, 3H), HPLC (tr/purity): 2888.98 min, >94%. ESI m/z (MeOH) 205.49 (MH+).

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