Iodoethane → Ethyl 6-fluoro-7-(pyrrol-1-yl)-1-formylethylamino-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 4568Notes

Reaction equation

HRID 4568 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH:16]=[CH:15][CH:14]=[CH:13]1)[N:8]([NH:17][CH:18]=O)[CH:7]=[C:6]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:5]2=[O:25].[C:26](=[O:29])([O-])[O-].[K+].[K+].[CH2:32](I)C>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH:16]=[CH:15][CH:14]=[CH:13]1)[N:8]([NH:17][CH:18]([CH:26]=[O:29])[CH3:32])[CH:7]=[C:6]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:5]2=[O:25]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 13670073Ethyl 6-fluoro-7-(pyrrol-1-yl)-1-formylamino-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 86742002Ethyl 6-fluoro-7-(pyrrol-1-yl)-1-formylethylamino-4-oxo-1,4-dihydroquinoline-3-carboxylateYield 37.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.5 g (0.005 mol) of ethyl 6-fluoro-7-(pyrrol-1-yl)-1-formylamino-4-oxo-1,4-dihydroquinoline-3-carboxylate and 1.3 g (0.01 mol) of potassium carbonate in 10 ml of dimethylformamide is stirred for 3 hours at room temperature, 2.35 g (0.015 mol) of ethyl iodide are then added and the mixture is kept for 4 hours at room temperature. It is poured into a water/ice mixture, the precipitate obtained is filtered off, washed with water and extracted with chloroform, the extract is washed with water, the organic layer is dried, the solvent is evaporated off and the residue is recrystallized from an ethanol/water mixture (1:1) to give 0.7 g of a solid melting at 192°-194° C.

Workup

  1. waitthe mixture is kept for 4 hours at room temperature
  2. customthe precipitate obtained
  3. filtrationis filtered off
  4. washwashed with water
  5. extractionextracted with chloroform
  6. washthe extract is washed with water
  7. customthe organic layer is dried
  8. customthe solvent is evaporated off
  9. customthe residue is recrystallized from an ethanol/water mixture (1:1)

Sources & evidence

ORD record
ord-7771b7d4dfd64e73b2d9da266949289a
Source dataset
uspto-grants-1988_02
Patent number
US04727080

Reaction notes

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