Water → HCID 14819728, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 9.0 g (0.020 mole) of methyl 3-[5- fluoro-4-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)-2-nitrophenyl]-2-bromopropionate in 100 mL of glacial acetic acid was stirred, and 9.0 mL of water was added. The reaction mixture was warmed to 40° C., and 9.0 g (0.16 mole) of iron powder was slowly added. Upon completion of addition the reaction mixture was allowed to cool to ambient temperature where it was stirred for 2 hours. The reaction mixture was filtered through a pad of diatomaceous earth. The filtrate was diluted with water, and the mixture was extracted with 100 mL of ethyl acetate. The filtrate was concentrated under reduced pressure to yield 7.5 g of 1-(3-bromo-6-fluoro-3,4-dihydroquinolin-2(1H)-one-7-yl)-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one as an oil. The nmr spectrum was consistent with the proposed structure.

Provenance & Evidence