Cl[C:2]1[N:3]=[N:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][CH:7]=1.C([O-])(=[O:17])C.[Na+].[OH-].[Na+]>C(O)(=O)C.O>[O:8]([C:5]1[CH:6]=[CH:7][C:2](=[O:17])[NH:3][N:4]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1A mixture of 3-chloro-6-phenoxy-pyridazine (1.01 g, 4.89 mmol) and sodium acetate (1.40 g, 17.06 mmol) in glacial acetic acid (50 mL, 0.1M) was heated to 110° C. overnight. After this time the reaction was cooled to 25° C. and was diluted with water (450 mL). The reaction was brought to pH=5-6 by the addition of a 5N aqueous sodium hydroxide solution. The resulting solution was extracted with ethyl acetate (3×100 mL). The combined organics were washed with a saturated aqueous sodium chloride solution (1×100 mL), dried over magnesium sulfate, filtered, rinsed with ethyl acetate and concentrated in vacuo. The resulting oil was azeotroped with methanol four times and dried in vacuo to afford 6-phenoxy-2H-pyridazin-3-one (0.78 g, 86%) as a white solid. 1H-NMR (300 MHz, DMSO-d6) δ ppm 7.00 (d, J=10.0 Hz, 1H), 7.13-7.27 (m, 3H), 7.34-7.46 (m, 3H), 12.29 (br s, 1H).
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