Phosphorus oxychloride → HCID 13535954, compound

Participants

Reaction Steps

To 150 ml of phosphorus oxychloride, at an internal temperature of 80°-85°, was added in portions, with vigorous stirring, during 0.5 hr, 40.5 g (0.184 mole) of 5-hydroxy-6-methoxy-8-nitroquinoline. After completion of addition, the mixture, which had turned from a red solution to a yellow suspension, was heated under reflux for 1.5 hr. The golden yellow solution was allowed to cool to room temperature and the resulting yellow mush was added to a vigorously stirred mixture of 700 ml of conc ammonium hydroxide and ice. The addition rate was regulated to keep the temperature from rising above 25° The pale yellow precipitate was washed with water and air dried to give 43 g (97%) of 5-chloro-6-methoxy-8-nitroquinoline mp 204°-206° (Mp 204° cited by R. C. Fuson et al., J. Org. Chem., 12, 799 (1947).

Provenance & Evidence