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

HRID 1681193Notes

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-70060ebe437443228ff369e7f564e37b
Source dataset: uspto-grants-1992_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05169853

Reaction notes

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