Sodium dithionate → 2-chloro-N4-pent-4-ynylquinoline-3,4-diamine

Participants

Reaction Steps

An aqueous solution (125 mL) of sodium dithionate (38.0 g, 218 mmol) was added to a solution of 2-chloro-3-nitro-N-pent-4-ynylquinolin-4-amine (12.64 g, 43.63 mmol) in ethanol (15 mL) and acetonitrile (130 mL). A fine white precipitate formed within seconds. After 2.5 hours, the volatiles were removed under reduced pressure leaving a yellow aqueous mixture that was diluted with water (1 L) and washed with dichloromethane (250 mL×3). The organic layers were combined, washed with water and brine, dried over magnesium sulfate, filtered, and concentrated to yield 2-chloro-N4-pent-4-ynylquinoline-3,4-diamine as an amber oil (8.10 g) that was used without further purification.

Provenance & Evidence