Iodoethane → HCID 13772822, compound

HRID 622533Notes

Reaction equation

HRID 622533 reaction equation
[C:1]([C:4]1[C:13]([F:14])=[C:12]2[C:7]([C:8](=[O:20])[C:9]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:10][NH:11]2)=[CH:6][C:5]=1[F:21])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:28](I)[CH3:29]>CN(C)C=O>[C:1]([C:4]1[C:13]([F:14])=[C:12]2[C:7]([C:8](=[O:20])[C:9]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:10][N:11]2[CH2:28][CH3:29])=[CH:6][C:5]=1[F:21])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 13772821HCID 13772821, compound

Product 1

HCID 13772822HCID 13772822, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

To 22.3 g (76.6 mmol) of the ethyl 7-acetyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate in 900 ml of dimethylformamide was added 25.6 g (2.5 eq) of potassium carbonate and 22 ml (3.6 eq) of ethyl iodide. The mixture was stirred at 45° C. overnight. The mixture was concentrated. The residue was dissolved in water and extracted into dichloromethane. The dichloromethane was concentrated and the residual oil was purified by column chromatography on silica gel to give 10.5 g of ethyl 7-acetyl-1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinoline carboxylate, mp 129°-130° C.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionThe residue was dissolved in water
  3. extractionextracted into dichloromethane
  4. concentrationThe dichloromethane was concentrated
  5. customthe residual oil was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-0f157435cde04aa3bab3dd968b785e80
Source dataset
uspto-grants-1988_09
Patent number
US04771054

Reaction notes

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