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Methyl iodide → ethyl 6,7-difluoro-1-(N-formylmethylamino)-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylate

HRID 358895
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 358895
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:13][CH3:14])[C:11]=1[F:12])[N:8]([NH:15][CH:16]=O)[CH:7]=[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:5]2=[O:23].[C:24](=O)([O-])[O-:25].[K+].[K+].CI>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:13][CH3:14])[C:11]=1[F:12])[N:8]([NH:15][CH2:16][CH:24]=[O:25])[CH:7]=[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:5]2=[O:23]
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Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 20067143Ethyl 6,7-difluoro-1-(formylamino)-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylate

Produkt 1

HCID 20067145ethyl 6,7-difluoro-1-(N-formylmethylamino)-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylateAusbeute 81,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

The whole (0.0018 mole) of the ethyl 6,7-difluoro-1-(formylamino)-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylate (XVI) [prepared as described in Step (D2) above] was dissolved in 8 ml of dimethylformamide. 0.51 g (0.0037 mole) of potassium carbonate and 0.78 g (0.0052 mole) of methyl iodide were then added to the solution, and the mixture was stirred at room temperature for 3 hours. At the end of this time, the solvent was distilled from the mixture under reduced pressure. The residue was extracted with chloroform, and the chloroform extract was washed with water, dried and concentrated by evaporation under reduced pressure to give 0.5 g of ethyl 6,7-difluoro-1-(N-formylmethylamino)-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylate (XVII, R10 =methyl) as a colorless powder.

Aufarbeitung

  1. distillationAt the end of this time, the solvent was distilled from the mixture under reduced pressure
  2. extractionThe residue was extracted with chloroform
  3. extractionthe chloroform extract
  4. washwas washed with water
  5. customdried
  6. concentrationconcentrated by evaporation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-86776ce3bbb34f7dbcc86142f0b92e09
Quelldatensatz
uspto-grants-1991_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04997943

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