Water → 8-Amino-6-methoxy-4-methyl-5-[7-phenylheptoxy]quinoline

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Reaction Steps

A stirred mixture of 6-methoxy-4methyl-8-nitro-5-(7-phenylheptoxy) quinoline [Example 1b](2.0 g, 0.005 mol) de-greased 40 mesh Fe filings (5 g) H2O (20 ml), HOAc (4 ml) and n-Bu2O was heated at 80°-85° C. for 1 h, cooled and filtered. The solid was thoroughly extracted with Et2O (500 ml) and the extract was dried (Na2SO4) treated with charcoal and concentrated to an oil. Crystallization from pet ether gave 1.6 g (85%) of 8-amino-6-methoxy-4-methyl-5-(7-phenylheptoxy) quinoline as yellow green crystals, mp 61°-63° C. A second crystallization from pet ether (Darco) provided the analytical sample as glistening yellow crystals, mp 64°-65° C.

Provenance & Evidence