Propylene Oxide → 6-Methoxy-4-methyl-8-nitro-5-(6-phenylhexoxy) quinoline

Participants

Reaction Steps

To a stirred mixture of 5-hydroxy-6-methoxy-4-methyl-8-nitroquinoline (2.3 g, 0.01 mole), 1-bromo-6-phenylhexane (2.4 g, 0.01 mole) and HMPA (25 ml), at 130° C., was added dropwise, during 2 h, a mixture of Et3N (1ml) and propylene oxide (9 ml). After four more hours, an additional 10 ml of the Et3N--propylene oxide mixture was introduced. Heating was continued for 24 h and 1.2 g (0.005 mole) of 1-bromo-6-phenylhexane was added followed by another 10 ml of Et3N--propylene oxide. This final mixture was heated for 6 h, allowed to cool, diluted with CHCl3 (50 ml), placed on a silica gel column and eluted with CHCl3. Concentration of the yellow eluate gave 2.3 g of 6-methoxy-4-methyl-8-nitro-5-(6-phenylhexoxy) quinoline as an oil which was used without further purification.

Provenance & Evidence