Propylene Oxide → 6-Methoxy-4-methyl-8-nitro-5-[4-phenylbutoxy]quinoline

Participants

Reaction Steps

To a stirred mixture of 5-hydroxy-6methoxy-4-methyl-8-nitroquinoline (5.9 g, 0.025 mol), 1-bromo-4-phenylbutane (4.3 g, 0.02 mol) and HMPA (15 ml), at 110°-115° C., was added dropwise, during 1 h, a mixture of propylene oxide (6 ml) and Et3N (1 ml). The reaction was continued for 5 h, allowed to cool and extracted successively with pet ether, Et2O and Me2CO leaving 1.1 g of insoluble starting material, 5-hydroxy-6-methoxy-4-methyl-8-nitroquinoline. The pet ether and Et2O fractions were worked up as described above for 6-methoxy-4-methyl-8-nitro-5-(7-phenylheptoxy)quinoline (see example 1, part b) to give crude 6-methoxy-4-methyl-8-nitro-5(4-phenylbutoxy) quinoline as an oil. This material was dissolved in CHCl3, placed on a silica gel column and eluted with CHCl3. The eluates were concentrated to an oil which on trituration with pet ether gave 3.2 g (43%) of 6-methoxy-4-methyl-8-nitro-5-(4-phenylbutoxy) quinoline as yellow-green crystals, mp 88°-89° C. Recrystallization from hexane provided the analytical sample, mp 90°-91° C.

Provenance & Evidence