To a stirred mixture of 5-hydroxy-6methoxy-4methyl-8nitroquinoline (4.7 g, 0.02 mol), 1 bromo-9-phenylnonane (4.2 g, 0.015 mol) and HMPA (10 ml), at 125- 130° C., was added dropwise, during 0.5 h, a mixture of propylene oxide (6 ml) and Et3N (1 ml). The reaction was continued for 6 h, allowed to cool and extracted successively with pet ether, Et2O and Me2CO leaving 1.9 g of insoluble starting material, 5-hydroxy-6-methoxy-4-methyl-8-nitroquinoline. The combined pet ether and Et2O extracts were washed (H2O, dil NaOH, H2O) dried (Na2SO4) and concentrated. The residual oil was dissolved in CHCl3, placed on a silica gel column (100 g) and eluted with CHCl3. The eluates were concentrated, triturated with pet ether and crystallized from Et2O (Darco) to give 2.1 g of 6-methoxy-4-methyl-8-nitro-5 -(9-phenylnonoxy) quinoline as yellow crystals, mp 56°-56.5° C. This material was used without further purification.
