Propylene Oxide → HCID 613143, compound

Participants

Reaction Steps

A stirred mixture of 5-hydroxy-6-methoxy-8-nitroquinoline, (6.6 g, 0.03 mole), n-octylbromide (6.7 g, 0.035 mole) and hexamethylphosphoric triamide (10 ml) was maintained at 125°-130°, under N2, while a mixture of triethylamine (1 ml) and propylene oxide (6 ml) was added in small portions during 3 hr. The mixture was cooled and extracted with petroleum ether (bp 20°-40°) (3×100 ml). The extracts were discarded. The petroleum ether-insoluble, semi-solid residue was dissolved in 300 ml of diethyl ether and washed with water, dilute sodium hydroxide and water. The ethereal solution was dried and concentrated in vacuo to leave 8 g of pale brown solid. Crystallization from boiling petroleum ether (20°-40°) (carbon) gave 7.5 g (75%) of the 5-octoxyquinoline derivative, mp 52°-54°. An additional crystallization from petroleum ether did not change the melting point.

Provenance & Evidence