Iodoethane → HCID 21473333, compound

HRID 2293983Notes

Reaction equation

HRID 2293983 reaction equation
[F:1][C:2]1[C:11]([O:12][CH:13]([F:15])[F:14])=[C:10]2[C:5]([C:6]([OH:21])=[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:28](I)[CH3:29]>CN(C)C=O>[CH2:28]([N:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([F:1])[C:11]=2[O:12][CH:13]([F:14])[F:15])[C:6](=[O:21])[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:8]1)[CH3:29]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 178469679HCID 178469679, compound

Product 1

HCID 21473333HCID 21473333, compoundYield 33.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

In 96 ml of N,N-dimethylformamide was dissolved 3.0 g (0.01 mole) of ethyl 7-fluoro-8-difluoromethoxy-4-hydroxyquinoline-3-carboxylate obtained as described above, and 6.9 g (0.05 mole) of potassium carbonate and 12.5 g (0.08 mole) of ethyl iodide were added thereto. The mixture was stirred at 100° C. for 14 hours. After completion of the reaction, the solvent was removed under reduced pressure, and water was added to the residue. Crystals precipitated were collected by filtration and applied to silica gel column chromatography (the eluent used was a mixture of chloroform:methanol=95:5) to obtain 1.1 g of ethyl 1-ethyl-7-fluoro-8-difluoromethoxy-1,4-dihydro-4-oxoquinoline-3-carboxylate as white crystals.

Workup

  1. customobtained
  2. additionwere added
  3. customAfter completion of the reaction
  4. customthe solvent was removed under reduced pressure, and water
  5. additionwas added to the residue
  6. customCrystals precipitated
  7. filtrationwere collected by filtration
  8. additiona mixture of chloroform

Sources & evidence

ORD record
ord-22d4cfdeaeec42f992947b2ba6164f3b
Source dataset
uspto-grants-1997_11
Patent number
US05688791

Reaction notes

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