Peak assignment in the 1H-NMR spectrum of 10 mM TAB2OH in 20 mM phosphate-pyrophosphate (+ 0.1 M NaCl) 2H2O buffer, pH 5
2-Trimethylammonio-6-hydroxy-benzaldehyde oxime chloride (TAB2OH)
To a stirring solution of 4.19 (90 mg, 0.50 mmol) in dichloromethane (0.2 ml) at 0°C was added methyl trifluoromethansulfonate (62 μl, 0.55 mmol). The reaction was allowed to warm to room temperature and stirred for 40 h. The precipitate formed was collected by filtration washing with excess dichloromethane to afford 101 mg of the pure triflate salt as a white solid (59%). The salt was dissolved in acetonitrile and a solution of tetrahexylammonium chloride in acetonitrile was added to precipitate the pure chloride salt as a white solid.
1H-NMR (600 MHz, d6-DMSO) δ 11.74 (s, 1 H), 10.95 (s, 1 H), 8.34 (s, 1 H), 7.45 (t, J 8.4 Hz, 1 H), 7.39 (d, J 8.4 Hz, 1 H), 7.26 (d, J 8.2 Hz, 1 H), 3.68 (s, 9 H).
13C-NMR (150.9 MHz, d6-DMSO) δ 158.9, 145.6, 145.5, 130.6, 117.5, 113.5, 111.3, 57.2.
HRMS (M+) expected, 195.1133; found, 195.1130.
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2-Dimethylamino-6-hydroxy-benzaldehyde oxime (4.19)
To a stirring solution of 2-dimethylamino-6-methoxymethoxy-benzaldehyde oxime (14 mg, 0.06 mmol) in methanol (0.2 ml) at room temperature was added a 4 M solution of hydrogen chloride in dioxane (0.2 ml, 0.8 mmol). The reaction was heated to 70°C for 1 h and then cooled to room temperature and the solvent was blown off with nitrogen. The crude material was purified by flash chromatography over silica gel eluting with dichloromethane to afford 10 mg of pure product as a white solid (91%). 1H-NMR (600 MHz, [2H]chloroform) δ 10.06 (s, 1 H), 8.65 (s, 1 H), 7.21 (t, J 8.1 Hz, 1 H), 7.11 (s, 1 H), 6.66 (d, J 8.2 Hz, 1 H), 6.60 (d, J 8.0 Hz, 1 H), 2.73 (s, 6 H). 13C-NMR (150.9 MHz, [2H]chloroform) δ 158.5, 154.8, 151.4, 131.6, 111.3, 110.2, 109.8, 45.6. HRMS (MH+) expected, 181.0971; found, 181.0983.
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