Chemical Properties
YELLOW CRYSTALLINE POWDER
Uses
6-Methoxy-8-nitroquinoline is used in treating and preventing pancreatic cancer. Also, used in preparation of Quinoline derivatives as antiparasitic agents useful in the prophylaxis and treatment of malaria and parasitic diseases.
Synthesis Reference(s)
Journal of the American Chemical Society, 68, p. 1569, 1946
DOI: 10.1021/ja01212a057Organic Syntheses, Coll. Vol. 3, p. 568, 1955
Synthesis
4-Methoxy-2-nitroaniline (20.0 g, 119 mmol) was mixed with glycerol (34.0 g, 369 mmol), 3-nitrobenzenesulfonic acid sodium salt (24.0 g, 107 mmol), water (25 mL), and concentrated sulfuric acid (34 mL), and the reaction was carried out at reflux for 12 hours. Upon completion of the reaction, the mixture was cooled to 45 °C, slowly poured into 1 L of cold water and stirred vigorously with dichloromethane (500 mL) for 30 min. The resulting two-phase solution was filtered through diatomaceous earth and the aqueous phase was extracted with dichloromethane (3 x 300 mL). The organic phases were combined, washed sequentially with water (400 mL) and saturated saline (400 mL), dried over anhydrous magnesium sulfate, filtered and concentrated to remove the solvent. The crude product was purified by silica gel column chromatography with hexane/ethyl acetate (4/1, v/v) as eluent to afford 6-methoxy-8-nitroquinoline (10.0 g, 49.0 mmol, 42% yield) as a brown solid. Mass spectrum (electrospray ionization) m/z 205 ([M+H]+).
References
[1] Patent: US2003/32645, 2003, A1
