Sodium Hydroxide → 5,7-Dichloro-6-fluoro-isoquinoline

Participants

Reaction Conditions

Reaction Steps

5 g (23.1 mmol) 7-Chloro-6-fluoro-isoquinoline (6) were dissolved in 90 ml conc. sulfuric acid. At room temperature 7.34 g (55 mmol) N-chlorosuccinimide were added. The solution was heated to 50° C. and another 3.67 g (27.5 mmol) N-chlorosuccinimide were added. After standing overnight at room temperature, the reaction was again heated to 50° C. and another 18.35 g (137.5 mmol) N-chlorosuccinimide were added during the next 8 h. For working up, the reaction mixture was poured on ice. The aqueous solution was adjusted to alkaline pH with sodium hydroxide. The precipitate was filtered off and extracted three times with dichloromethane. The dichloromethane phases were dried with magnesium sulfate and evaporated to yield 1.09 g of the title compound, which was used without further purification.

Provenance & Evidence