Ethanol → HCID 70607702, compound

Participants

Reaction Steps

A mixture of 7.5 g (0.014 mole) 2-(4-chlorobenzyloxy)-6-methoxy-8-(4-phthalimido-1-methylbutylamino)quinoline (crude), 6.0 ml 85% hydrazine hydrate, and 100 ml 95% ethanol was refluxed 3 hr. After standing overnight, the mixture was stirred with ether and 20 g 50% aq. KOH. The ether layer was washed with water and sat'd. brine. The aqueous portions were extracted with ether and the washing process repeated. A sat'd solution of 2.0 g maleic acid in methanol was added to the dried (MgSO4) ether solution. There was obtained 5.10 g (71%) of an off-white solid, mp 173°-177°. Recrystallization of the crude maleate from 120 ml 95% ethanol (charcoal) afforded 3.55 g, mp 174°-178°. Further recrystallization from ethanol gave the analytical sample, mp 176°-177.5°.

Provenance & Evidence