Propanoyl bromide, 2-bromo- → 6-(2-Bromo-1-oxopropyl)-8-chloro-3,4-dihydro-2(1H)-quinolinone

Participants

Reaction Steps

To a solution of α-bromopropionyl bromide (60 g) and aluminum chloride (40 g) in carbon disulfide (100 ml) was added 8-chloro-3,4-dihydrocarbostyril (10 g). After refluxing the mixture for 5 hours, carbon disulfide was evaporated and heated at 70° to 80° C. for 5 hours. The reaction mixture was poured into ice water and allowed to stand overnight. The mixture was extracted with chloroform and the chloroform layer was washed with water, dried and treated with activated carbon followed by evaporating chloroform. The residue was washed with diethyl ether and collected by filtration. The residue gave uniform crude crystals upon TLC. The crystals thus obtained were re-crystallized from methanol to give 12 g of 8-chloro-6-α-bromopropionyl-3,4-dihydrocarbostyril.

Provenance & Evidence