6-Methoxyquinoline-iV-oxide

Similarly, amines can be installed at the 2-position of 6-methoxyquinoline-iV-oxide. Addition of t-butylamine in the presence of toluenesulfonic anhydride furnishes 2-substituted quinoline, which can be converted to the primary amine by treat-... 

On treatment of both quinoline and pyridine /V-oxides with bromine and thallium(iil) acetate, y-bromo-derivatives are formed pyridine JV-oxides are the less reactive substrates/ The reaction of 8-methoxyquinoline iV-oxide with acetic anhydride and methanol yields 84% of 2,8-dimethoxyquinoline. Similarly, the reaction of the 6-methoxy-iV-oxide and ethanol and acetic anhydride gives 2-ethoxy-6-methoxyquinoline, but, under the same conditions, the 7-methoxy-N-oxide is unchanged/ The Reissert compounds (149) derived from substituted quinolines, on treatment with thallium(lll) nitrate and trimethyl orthoformate, undergo either smooth ring-contraction or oxidative debenzoyl-ation, depending on the substitution pattern in the aromatic ring (Scheme 61)/ ... 

Disposition in the Body. Readily absorbed after oral administration. It is extensively metabolised by oxidation to carboxyprimaquine which is the major plasma metabolite. Other reactions which may occur are demethylation and oxidation to the 5,6-diol, which is then converted to an active quinone, V-dealkylation to 8-amino-6-methoxyquinoline, and iV-acetyla-tion. Less than 5% of a dose is excreted in the urine unchanged in 24 hours. 

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