Iodoethane → 1-Ethyl-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, ethyl ester

HRID 542477Notes

Reaction equation

HRID 542477 reaction equation
[F:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:20])[C:5]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:6][NH:7]2.C(=O)([O-])[O-].[K+].[K+].[CH2:27](I)[CH3:28]>CN(C)C=O>[CH2:27]([N:7]1[C:8]2[C:3](=[C:2]([F:1])[C:11]([F:12])=[C:10]([F:13])[C:9]=2[F:14])[C:4](=[O:20])[C:5]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:6]1)[CH3:28]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 138510175,6,7,8-Tetrafluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, ethyl ester

Product 1

HCID 138510181-Ethyl-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 38.5 g (134 mmol) of 5,6,7,8-tetrafluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, ethyl ester in 700 ml of N,N-dimethylformamide was added 37.15 g (two equivalents) of potassium carbonate and 50 ml (five equivalents) of ethyl iodide. The mixture was brought to 50° C. and stirred vigorously overnight. The solvents were removed and the residue partioned between water and dichloromethane. The dichloromethane was dried (magnesium sulfate) and concentrated. The residue was triturated with diethyl ether to give 30.5 g of material which was recrystallized from ethanol. Filtration gave 23.5 g of the title compound, mp 217°-220° C.

Workup

  1. customwas brought to 50° C.
  2. customThe solvents were removed
  3. dry with materialThe dichloromethane was dried (magnesium sulfate)
  4. concentrationconcentrated
  5. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-59bd5c858c12409cb1932b5f5a8f4f7d
Source dataset
uspto-grants-1987_04
Patent number
US04657913

Reaction notes

Loading…