Water → 8-Amino-6-methoxy-4-methyl-5-(4-phenylbutoxy)quinoline

Participants

Reaction Steps

A stirred mixture of 6-methoxy-4-methyl-8-nitro-5-(4-phenylbutoxy) quinoline (3.7 g, 0.01 mol), degreased 40 mesh Fe filings (10 g), H2O (40 ml), HOAc (8 ml) and Bu2O (8 ml) was heated at 80°-100° C. for 2.5 h, allowed to cool and filtered. The solid was thoroughly extracted with Et2O and the extract was dried (Na2SO4), treated with carbon and concentrated to an oil. Extraction of the latter with pet ether and cooling the extract gave 2.2 g (66%) of 8-amino-6-methoxy-4-methyl-5-(4-phenylbutoxy)quinoline as yellow-green crystals, mp 59°-59.5° C. Recrystallization from pet ether afforded the analytical sample as yellow crystals, mp 60°-61° C.

Provenance & Evidence