Iodoethane → HCID 13958509, compound

HRID 255982Notes

Reaction equation

HRID 255982 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[C:12]1[CH:17]=[C:16]([CH3:18])[N:15]=[C:14]([CH3:19])[CH:13]=1)[NH:8][CH:7]=[C:6]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:5]2=[O:25].C(=O)([O-])[O-].[K+].[K+].[CH2:32](I)[CH3:33]>CN(C)C=O>[CH2:32]([N:8]1[C:9]2[C:4](=[CH:3][C:2]([F:1])=[C:11]([C:12]3[CH:17]=[C:16]([CH3:18])[N:15]=[C:14]([CH3:19])[CH:13]=3)[CH:10]=2)[C:5](=[O:25])[C:6]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:7]1)[CH3:33]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 13958726HCID 13958726, compound

Product 1

HCID 13958509HCID 13958509, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture containing 34 g of ethyl 6-fluoro-1,4-dihydro-7-(2,6-dimethyl-4-pyridinyl)-4-oxo-3-quinolinecarboxylate, finely divided anhydrous potassium carbonate and 250 ml of dimethylformamide was heated with stirring on a steam bath for 20 minutes and then 9 ml of ethyl iodide was added over a 20 minute period. The reaction mixture was heated on a steam bath with stirring for 2 and 1/2 hours and then concentrated to dryness on a rotary evaporator. The residue was shaken well with 300 ml of water and 500 ml of chloroform. The layers were separated and the aqueous layer was extracted with another 200 ml portion of chloroform. The combined chloroform extracts were concentrated in vacuo to remove the chloroform. The remaining solid was dissolved in 150 ml of hot isopropyl alcohol, the hot solution treated with decolorizing charcoal and filtered. The filtrate was concentrated on a rotary evaporator to a volume of about 50 ml which was diluted with ether until turbid. The mixture was allowed to cool and the separated crystalline solid was collected, washed with ether and dried at 80°-85° C. to yield 18.5 g of ethyl 1-ethyl-6-fluoro-1,4-dihydro-7-(2,6-dimethyl-4-pyridinyl)-4-oxo-3-quinolinecarboxylate, m.p. 221°-224° C. Further concentration of the mother liquor yielded another 3.4 g (60%) of product, m.p. 220°-223° C. A larger run (0.3 mole scale) gave the above compound, m.p. 222°-225° C., in 80% yield.

Workup

  1. temperaturewas heated
  2. temperatureThe reaction mixture was heated on a steam bath
  3. stirringwith stirring for 2 and 1/2 hours
  4. concentrationconcentrated to dryness on a rotary evaporator
  5. stirringThe residue was shaken well with 300 ml of water and 500 ml of chloroform
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted with another 200 ml portion of chloroform
  8. concentrationThe combined chloroform extracts were concentrated in vacuo
  9. customto remove the chloroform
  10. dissolutionThe remaining solid was dissolved in 150 ml of hot isopropyl alcohol
  11. additionthe hot solution treated with decolorizing charcoal
  12. filtrationfiltered
  13. concentrationThe filtrate was concentrated on a rotary evaporator to a volume of about 50 ml which
  14. additionwas diluted with ether until turbid
  15. temperatureto cool
  16. customthe separated crystalline solid was collected
  17. washwashed with ether
  18. customdried at 80°-85° C.

Sources & evidence

ORD record
ord-8797799fe44446e889eedfedf161dd58
Source dataset
uspto-grants-1987_10
Patent number
US04699984

Reaction notes

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