[NH2:1][OH:2].Cl.CC(O[Na])=O.[CH3:9][NH:10][C:11]1([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=2[Cl:24])[C:16](=O)[CH2:15][CH2:14][CH2:13][CH2:12]1>CO.O.O>[Cl:24][C:23]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:11]1([NH:10][CH3:9])[CH2:12][CH2:13][CH2:14][CH2:15][C:16]1=[N:1][OH:2]To as solution of NH2OH. HCl and CH3COONa. H2O in MeOH:H2O (7:3) stirred at room temperature for 15 minutes, was added ketamine and the resulting solution was stirred at reflux for 16 hrs before cooling to room temperature. The reaction mixture was filtered and the filtrate was partitioned between CH2Cl2 and sat. NaHCO3 solution. The filtrate was extracted with CH2Cl2 (2×30 mL) and the combined organic layer was washed with brine solution. The organic layer was dried over anhydrous. Na2SO4 and concentrated under reduced pressure. The crude reaction mixture received was purified over silica gel column chromatography by eluting with initially CH2Cl2 and later with (1:9) MeOH:CH2Cl2 to receive oxime 2 as pale yellow solid. 1H NMR (250 MHz, CDCl3) δ 7.4-7.5 (m, 1H), 7.0-7.3 (m, 3H), 2.6-2.8 (m, 1H), 2.4-2.5 (q, J=5.8 Hz, 1H), 2.1-2.3 (m, 1H), 2.0-2.1 (m, 3H), 1.5-1.7 (m, 5H). 13C NMR (63 MHz, CDCl3) δ 160.1, 140.1, 133.8, 131.6, 129.1, 128.1, 126.5, 64.0, 37.1, 29.4, 24.5, 22.2, 21.7.
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