Water → HCID 14819728, compound

HRID 329896Notes

Reaction equation

[F:1][C:2]1[C:3]([N:18]2[C:22](=[O:23])[N:21]([CH:24]([F:26])[F:25])[C:20]([CH3:27])=[N:19]2)=[CH:4][C:5]([N+:15]([O-])=O)=[C:6]([CH2:8][CH:9]([Br:14])[C:10](OC)=[O:11])[CH:7]=1.O>C(O)(=O)C.[Fe]>[Br:14][CH:9]1[CH2:8][C:6]2[C:5](=[CH:4][C:3]([N:18]3[C:22](=[O:23])[N:21]([CH:24]([F:26])[F:25])[C:20]([CH3:27])=[N:19]3)=[C:2]([F:1])[CH:7]=2)[NH:15][C:10]1=[O:11]

Participants

Conditions

Temperature: 40 °C

Procedure

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.

Workup

additionUpon completion of addition the reaction mixture
temperatureto cool to ambient temperature where it
filtrationThe reaction mixture was filtered through a pad of diatomaceous earth
additionThe filtrate was diluted with water
extractionthe mixture was extracted with 100 mL of ethyl acetate
concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-069ad0b027944ff38ea89f5d6b0d145f
Source dataset: uspto-grants-1990_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04894084

Reaction notes

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