Propylene Oxide → HCID 613141, compound

Participants

Reaction Steps

To a stirred mixture of 15 g (0.068 mole) of 5-hydroxy-6-methoxy-8-nitroquinoline, 16.8 g (0.14 mole) of n-propyl bromide, 1.5 g of triethylamine and 20 g of hexamethylphosphoric triamide, heated at a bath temperature of 110°, was added dropwise, during 2 hr, 20 g of propylene oxide. After an additional 48 hr at 110° the green-brown mixture was poured into 150 ml of water. The aqueous mixture was extracted with diethyl ether and the extract was dried (magnesium sulfate) and concentrated to give a dark yellow residue. Crystallization from hexane provided 11.1 grams (62%) of 6-methoxy-8-nitro-5-(n-propoxy)quinoline as yellow crystals, mp 100°-104°. Recrystallization from methanol gave an analytical sample as pale yellow crystals, mp 101°-103°.

Provenance & Evidence