Potassium Carbonate → Ethyl 6-fluoro-7-(pyrrol-1-yl)-1-fluoroethyl-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 4564

Reaction equation

HRID 4564 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH:16]=[CH:15][CH:14]=[CH:13]1)[N:8]=[CH:7][C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:5]2[OH:22].C(=O)([O-])[O-].[K+].[K+].Br[CH:30]([F:32])[CH3:31]>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH:16]=[CH:15][CH:14]=[CH:13]1)[N:8]([CH:30]([F:32])[CH3:31])[CH:7]=[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:5]2=[O:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 235106171-Bromo-1-fluoroethaneHCID 178418515HCID 178418515, compound

Product 1

HCID 70417321Ethyl 6-fluoro-7-(pyrrol-1-yl)-1-fluoroethyl-4-oxo-1,4-dihydroquinoline-3-carboxylateYield 61.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3.2 g (0.011 mol) of ethyl 6-fluoro-7-(pyrrol-1-yl)-4-hydroxyquinoline-3-carboxylate and 4 g (2.5×0.011 mol) of potassium carbonate in 20 ml of dimethylformamide is heated for 30 minutes at 60° C. and left to cool, 7 g (5×0.011 mol) of bromofluoroethane are added, the mixture is kept for 7 hours at 80° C., left to cool and poured into a water/ice mixture, and the precipitate formed is filtered off, washed with water and recrystallized from a dimethylformamide/water mixture (1:1) to give 2.35 g of a solid melting at 231°-234° C.

Workup

  1. waitleft
  2. temperatureto cool
  3. waitleft
  4. temperatureto cool
  5. customthe precipitate formed
  6. filtrationis filtered off
  7. washwashed with water
  8. customrecrystallized from a dimethylformamide/water mixture (1:1)

Sources & evidence

ORD record
ord-961546021a8f448e97a2a1b9f8a02a55
Source dataset
uspto-grants-1988_02
Patent number
US04727080

Linked notes

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