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

HRID 128522Notes

Reaction equation

HRID 128522 reaction equation
[Br:1][C:2]1[C:20]([F:21])=[C:19]([F:22])[C:18]([F:23])=[C:17](F)[C:3]=1[C:4]([C:6](=[CH:12][NH:13][CH:14]1[CH2:16][CH2:15]1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].[F-].[Na+].O>CN(C)C=O>[Br:1][C:2]1[C:20]([F:21])=[C:19]([F:22])[C:18]([F:23])=[C:17]2[C:3]=1[C:4](=[O:5])[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:12][N:13]2[CH:14]1[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 962WaterHCID 5235Sodium FluorideHCID 178471892HCID 178471892, compound

Product 1

HCID 22924353Ethyl 5-bromo-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

28 g (68 mmol) of ethyl 2-(2-bromo-3,4,5,6-tetrafluoro-benzoyl)-3-cyclopropylamino-acrylate are heated under reflux in 88 ml of dimethylformamide with 6.9 g (164 mmol) of sodium fluoride for 6 hours. After cooling, the mixture is poured into water and the precipitate (red) which has separated out is filtered off with suction, washed with a large quantity of water and dried at 80° C. in a circulating air cabinet.

Workup

  1. temperatureAfter cooling
  2. customthe precipitate (red) which has separated out
  3. filtrationis filtered off with suction
  4. washwashed with a large quantity of water
  5. customdried at 80° C. in a circulating air cabinet

Sources & evidence

ORD record
ord-e75ed450e6934d37becfb1d2c4a6a8dc
Source dataset
uspto-grants-1995_11
Patent number
US05464796

Reaction notes

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