Phosphorus oxychloride → 4,6-Dichloro-3-nitroquinoline

Participants

Reaction Steps

11 g (48.97 mmol) of 6-chloro-3-nitro-quinolin-4-ol (step b) in 80 ml of POCl3 are heated under reflux for 5 h (tlc-control). The cool reaction mixture is poured slowly into 1.5 l of ice water. The title compound separates as a solid. The mixture is stirred for 15 min, the temperature not exceeding 0-5° C. The solid is filtered off, washed with water and dissolved in 200 ml ethylacetate. The organic phase is washed with a mixture of 200 ml of water and 38 ml of a 2 N sodium hydroxide solution, then again with water. After drying over MgSO4, the solvent is evaporated almost to dryness; hexane is added to the residue and the title compound is isolated by filtration as a dark-grey powder. This material is used in the next step without further purification.

Provenance & Evidence