O=P(Cl)(Cl)Cl.[Cl:6][C:7]1[CH:8]=[C:9]([C:13](=O)[CH3:14])[CH:10]=[CH:11][CH:12]=1.[ClH:16].NO.O.C[N:21]([CH:23]=O)C>>[Cl:16][C:13]([C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([Cl:6])[CH:8]=1)=[CH:14][C:23]#[N:21]A solution of POCl3 was slowly added to anhydrous DMF over a period of 20 minutes and the temperature was maintained around 30° C. 3′-Chloroacetophenone solution in anhydrous DMF was added to the above solution and the reaction temperature was allowed to rise to around 50° C. Hydroxylamine HCl was added to the reaction solution, portionwise, over 1 hour. A volume of 500 mL of water was added to form precipitate, stirred for 1 hour and the precipitate was collected on a Buchner funnel, washed with H2O, and dried to afford a yellow crystalline compound, mp 60-62° C. 1H NMR (DMSO-d6) δ1.60 (s, 6H), 7.30 (d, 1H, J=8.41 Hz), 7.41 (d, 1H, J=8.41 Hz), 10.47 (s, 1H); MS(+APCI)m/z 213(M+H); Anal. Calc. For C9H9ClN2O2: C, 50.84; H, 4.27; N, 13.17. Found: C, 50.99; H, 4.28; N, 12.98.
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