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36
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70449719543
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To a slurry solution of 4-aminotoluene (1.07 g, 0.01 mol) in 3 mL water was added slowly 6 mL of 37% HCl at 0-5 °C with stirring. Then, 20 mL of 20% NaNO2 was added to the mixture and the resulting solution was stirred for 1 h to give a bright yellow solution. 8-Hydroxyquinoline-5-sulfonic acid (2.25 g, 0.01 mol) was dissolved in the solution of Na2CO3 (4 M, 25 mL, which was added dropwise to the bright yellow solution above within 1 h. After stirring for 4 h, the reaction mixture was neutralized with HCl. The scarlet solid was filtered and recrystallized from ethanol to afford a pure product (2.7 g, 78.7, 1H NMR (DMSO-d6, 400 MHz, δ 2.42 (s, 3H, CH3, 7.42 (d, 2H, J, 8.0 Hz, ArH, 7.71 (q, 1H, J, 12.4 Hz, ArH, 7.91 (d, 2H, J, 8.4 Hz, ArH, 8.31 (s, 1H, ArH, 8.94 (d, 1H, J, 4.0 Hz, ArH, 9.14 (d, 1H, J, 8.4 Hz, ArH, 13C NMR DMSO-d6, 100 MHz, δ 23.83, 118.77, 125.14, 126
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4S: C, 55.97; H, 3.82; N, 12.24. Found: C, 55.80; H, 3.96; N, 12.38.
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37
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70449725482
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An ethanol solution (25 mL) of HQ (0.1 mmol, 34 mg) and an aqueous solution (3 mL) of CuSO4·5H2O (0.05 mmol, 12 mg) were mixed and refluxed for 3 h. The resulted dark-red solid was filtered, then washed with ethanol 3 × 3 mL, and dried under vacuum. Yield: 74, Anal. Calcd for C32H24CuN6O8S2: C, 51.37; H, 3.23; N, 11.23. Found: C, 51.02; H, 3.57; N, 11.02
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2: C, 51.37; H, 3.23; N, 11.23. Found: C, 51.02; H, 3.57; N, 11.02.
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46949104886
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Scarpa, M.6
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