Iodoethane → Ethyl 1-ethyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 2165619Notes

Reaction equation

HRID 2165619 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][C:12]([F:17])=[C:11]([F:18])[CH:10]=2)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:25](I)[CH3:26]>CN(C)C=O>[CH2:25]([N:8]1[C:9]2[C:14](=[CH:13][C:12]([F:17])=[C:11]([F:18])[CH:10]=2)[C:15](=[O:16])[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:7]1)[CH3:26]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 178469610HCID 178469610, compound

Product 1

HCID 854165Ethyl 1-ethyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A 20 g portion of the above ester was suspended in 400 ml of dimethylformamide, 27.3 g of potassium carbonate was added and this mixture was stirred at 90° C. A 61.8 g portion of ethyl iodide was added and this mixture was stirred at 90° C. for 24 hours and then evaporated. The residue was dissolved in water and then extracted with dichloromethane. The extract was washed with water, dried, filtered and evaporated in vacuo. The residue was recrystallized from ethanol, giving 16.15 g of 1-ethyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, ethyl ester.

Workup

  1. stirringthis mixture was stirred at 90° C. for 24 hours
  2. customevaporated
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted with dichloromethane
  5. washThe extract was washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-585bd26b841f496a9c6ea1d1266d2175
Source dataset
uspto-grants-1990_07
Patent number
US04940710

Reaction notes

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