Sodium Hydroxide → 6-Chloro-2-methyl-5-nitroquinoline

Participants

Reaction Steps

6-Chloroquinaldine (11 g) was dissolved in 15 ml of concentrated sulfuric acid and the solution was ice-cooled. Then, a solution of 7.1 g of potassium nitrate dissolved in 20 ml of concentrated sulfuric acid was added to the solution dropwise, during which operation the reaction temperature was maintained at 10° C. or less. After completion of addition the mixture was agitated at the same temperature as above for 1 hour and then poured onto 200 g of ice. Subsequently, the mixture was rendered alkaline with 10% sodium hydroxide, taking care that the internal temperature should not be raised to above 20° C., thus forming a pale yellow precipitate. The precipitate was collected by filtration, washed with water and recrystallized from ethanol to obtain 12.3 g of 5-nitro-6-chloroquinaldine as pale yellow rhombic crystals having a melting point of 123° to 124° C.

Provenance & Evidence