Iodoethane → HCID 13772822, compound

HRID 978551Notes

Reaction equation

HRID 978551 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-1a42f9575ddf4150844f48f81dd52d98
Source dataset
uspto-grants-1987_05
Patent number
US04665079

Reaction notes

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