反应详情

To a stirred mixture of 5-hydroxy-6-methoxy-4-methyl-8-nitroquinoline (4.98 g, 0.02 mol), 1-bromo-8-phenyloctane (4.7 g, 0.017 mol) and HMPA (13 ml), at 120° C., was added, dropwise, during 1 h, a mixture of propylene oxide (6 ml) and Et3N (1 ml). The reaction was continued for 3.5 h, allowed to cool and extracted successively with pet ether, Et2O and Me2CO leaving 1 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 residue was dissolved in CHCl3, placed on silica gel column and eluted with CHCl3. Concentration of the eluates left an oil which was triturated with pet ether to give 4.35 g (60%) of 6-methoxy-4-methyl-8-nitro-5-(8-phenyloctoxy) quinoline as yellow solid, mp 39.5°-41° C. Crystallization from hexane (Darco) provided the analytical sample as yellow crystals, mp 41°-42° C.

1. additionat 120° C., was added
2. waitThe reaction was continued for 3.5 h
3. temperatureto cool
4. extractionextracted successively with pet ether, Et2O and Me2CO
5. customleaving 1 g
6. washThe combined pet ether and Et2O extracts were washed (H2O, dil NaOH, H2O)
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated
9. dissolutionThe residue was dissolved in CHCl3
10. washeluted with CHCl3
11. waitConcentration of the eluates left an oil which
12. customwas triturated with pet ether