O.[C:2]1(C)[C:3]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:5]=[CH:6][CH:7]=1.[OH:13][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:23]=1[N:22]=[CH:21][CH:20]=[CH:19]2.[CH3:24]COCC>C(#N)C>[OH:13][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:23]=1[NH+:22]=[CH:21][CH:20]=[CH:19]2.[CH3:24][C:6]1[CH:5]=[CH:4][C:3]([S:8]([OH:11])(=[O:9])=[O:10])=[CH:2][CH:7]=1The toluenesulfonic acid salt of 8-hydroxyquinoline was formed by dissolving toluenesulfonic acid monohydrate (1.9 g, 10 mmol) in acetonitrile and adding 8-hydroxyquinoline (1.45 g, 10 mmol). Removal of solvent in vacuo and addition of ether to the residual oil results in crystallization. Trituration several times with ether followed by drying in vacuo yields 8-hydroxyquinolinium, p-toluenesulfonate as a powder (3.11 g).
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