Propylene Oxide → HCID 13535931, compound

Participants

Reaction Steps

A stirred mixture of 5-hydroxy-6-methoxy-8-nitroquinoline (22 g, 0.1 mole), n-hexyl bromide (18.5 g, 0.11 mole), triethylamine (1 g) and hexamethylphosphoric triamide (16 ml) was maintained at a bath temperature of 120°-130° while 10 g of propylene oxide was added during 0.5 hr. The mixture was heated at a bath temperature of 130°-145° for 3 hr and 5 more grams of propylene oxide was added. After 8 hr at 110°-120°, a low-boiling fraction was distilled off at 100° (1 atm) and the residue was cooled and poured into 3 liters of ice water. The resulting dull red solid was filtered and extracted with diethyl ether (2.5 g of 5-hydroxy compound was recovered as a diethyl ether-insoluble red solid). The ether extract was washed with dilute sodium hydroxide and water, dried (sodium sulfate) and concentrated to leave a thick oil. Trituration with petroleum ether (bp 20°-40°) gave 19.5 g (65%) of the required 5-hexoxy-quinoline derivative as a tan solid, mp 46°-49°. Crystallization from aqueous methanol (carbon) provided an analytical sample as yellow needles, mp 53°-55°.

Provenance & Evidence