[Br-].[CH:2]12[C:14](=[N+:15]3CCCC3)[CH:11]([CH2:12][CH2:13]1)[CH2:10][C:9]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:3]2.O.Cl.NO.O.O.O.C([O-])(=[O:29])C.[Na+]>CCO>[CH:2]12[C:14](=[N:15][OH:29])[CH:11]([CH2:12][CH2:13]1)[CH2:10][C:9]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:3]2
1-Tricyclo[8.2.1.03,8]trideca-3(8),4,6-trien-13-ylidene-pyrrolidinium bromide (48.14 g, 0.15 mol) was suspended in EtOH (200 mL) and H2O (100 mL) and stirred. Hydroxylamine hydrochloride (31.27 g, 0.45 mol) was added, resulting in the starting material dissolving. Sodium acetate trihydrate (61.2 g, 0.45 mol) was added to the solution. After a few minutes a thick white precipitate formed. The mixture was heated to reflux until a clear solution was obtained and then allowed to cool to room temperature. The product oxime crystallized from solution and was filtered off, washing with water. The resulting pure oxime was dried to give 27.18 g (90%) of a pure white crystalline solid. 1H NMR (d6-DMSO, 360 MHz) δ 10.17 (1 H, s, N—OH), 7.19-7.12 (4 H, m, aromatic), 3.51 (1 H, bt, bridgehead CH), 3.01-2.87 (2 H, m, benzylic), 2.80 (1 H, bt, bridgehead CH), 2.77 (2 H, t, J=14 Hz, benzylic), 1.68-1.63 (2 H, m), 1.10-1.05 (2 H, m). m/z 202 (M+H+).
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