Water → Ethyl 7-bromo-1-cyclopropyl-5,6,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 1461384Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[C:26]([F:27])=[C:25](F)[C:11]([C:12]([C:14](=[CH:20][NH:21][CH:22]2[CH2:24][CH2:23]2)[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:13])=[C:10]([F:29])[C:9]=1[F:30].O>CN(C)C=O>[Br:7][C:8]1[C:26]([F:27])=[C:25]2[C:11]([C:12](=[O:13])[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:20][N:21]2[CH:22]2[CH2:24][CH2:23]2)=[C:10]([F:29])[C:9]=1[F:30]

Participants

Conditions

Temperature: 150 °C

Procedure

Potassium carbonate (30 g) was added to a stirred solution/suspension of 31.65 g ethyl 2-(4-bromo-2,3,5,6-tetrafluorobenzoyl)-3-cyclopropylaminopropenoate in 300 ml dimethylformamide. The mixture was heated at 150° C. for 1.5 hours, then cooled, poured into water and extracted with methylene dichloride. The extract was washed with water and sodium chloride solution, dried (magnesium sulfate) and concentrated. The residue was recrystallized from acetonitrile to give 19.3 g (64%) ethyl 7-bromo-1-cyclopropyl-5,6,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate, m.p. 187°-189° C.

Workup

temperaturecooled
extractionextracted with methylene dichloride
washThe extract was washed with water and sodium chloride solution
dry with materialdried (magnesium sulfate)
concentrationconcentrated
customThe residue was recrystallized from acetonitrile

Sources & evidence

ORD record: ord-b4161097d0fd41f6a9244f3c2a4717bf
Source dataset: uspto-grants-1991_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05075319

Reaction notes

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