Iodoethane → Ethyl 7-chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylate

HRID 248457Notes

Reaction equation

HRID 248457 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:17])=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:8]=[N:9]2)=[CH:4][C:3]=1[F:18].C(=O)([O-])[O-].[CH2:23](I)[CH3:24]>CN(C)C=O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:17])[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][N:9]2[CH2:23][CH3:24])=[CH:4][C:3]=1[F:18]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 19660Carbonate IonHCID 3018009Ethyl 7-chloro-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 12733855Ethyl 7-chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 59.7 g portion of the above ester was suspended in 425 ml of dimethylformamide, 76.6 g of pctassium carbonate was added and this mixture was stirred in an oil bath at 80°-90° C. An 89 ml portion of ethyl iodide was added, the mixture was stirred at 80°-90° C. for 18 hours and then evaporated. The residue was dissolved in water and then extracted with dichloromethane. The extract was washed with water, dried, filtered through hydrous magnesium silicate and evaporated in vacuo. The solid was recrystallized from ethanol, giving 38 g of 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, ethyl ester.

Workup

  1. stirringthe mixture was stirred at 80°-90° C. for 18 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 through hydrous magnesium silicate
  8. customevaporated in vacuo
  9. customThe solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-6c7f721e79ef4d0ea1647af4db81e93b
Source dataset
uspto-grants-1993_05
Patent number
US05210193

Reaction notes

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