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

HRID 358675Notes

Reaction equation

HRID 358675 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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°.

Workup

  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)

Sources & evidence

ORD record
ord-5899096f2b07466f8aa64790839cd599
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

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