Sodium Hydroxide → 8-Fluoro-1-methyl-4-oxo-1,4-dihydroquinol-3-yl methanesulphonate

HRID 358675Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 358675
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[F:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]([CH3:17])[CH:14]=[C:13]([OH:18])[C:12]2=[O:19].[OH-].[Na+]>O>[CH3:1][S:2]([O:18][C:13]1[C:12](=[O:19])[C:11]2[C:16](=[C:7]([F:6])[CH:8]=[CH:9][CH:10]=2)[N:15]([CH3:17])[CH:14]=1)(=[O:4])=[O:3]

Komponenten

5

Edukt 3

HCID 14798Sodium Hydroxide3×HCID 31297Methanesulfonyl chloride2×HCID 231281098-Fluoro-3-hydroxy-1-methyl-4-quinolone

Produkt 1

HCID 537406098-Fluoro-1-methyl-4-oxo-1,4-dihydroquinol-3-yl methanesulphonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Methanesulphonyl chloride (1.1 g) d to a solution of 8-fluoro-3-hydroxy-1 -methyl-4-quinolone (1.83 g) and sodium hydroxide (0.6 g) in water (15 ml) and the resultant mixture stirred at 0 to 5° for 3 hours with the pH being adjusted to 9 after 20 minutes using aqueous sodium hydroxide (5M, 2 ml). Further methanesulphonyl chloride (1.1 g) was then added and the mixture stirred for 105 minutes whilst maintaining the pH at 9 by the addition of aqueous sodium hydroxide (5M, 2ml). The resultant solid was collected by filtration, washed with water (20 ml) and crystallised from industrial methylated spirit (100 ml) to give the novel compound 8-fluoro-1-methyl-4-oxo-1,4-dihydroquinol-3-yl methanesulphonate, m.p. 207°-209°.

Aufarbeitung

  1. temperaturewhilst maintaining the pH at 9
  2. filtrationThe resultant solid was collected by filtration
  3. washwashed with water (20 ml)
  4. customcrystallised from industrial methylated spirit (100 ml)

Quellen und Nachweise

ORD-Eintrag
ord-5899096f2b07466f8aa64790839cd599
Quelldatensatz
uspto-grants-1991_03
Patentnummer
US04997840

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