Sodium Hydroxide → Methyl-4-oxo-1,4-dihydroquinol-3-yl methanesulphonate

HRID 358667Notes

Reaction equation

HRID 358667 reaction equation
F[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:14])[C:7]([OH:13])=[CH:8][N:9]2[CH3:12])=[CH:4][CH:3]=1.[OH-].[Na+].[CH3:17][S:18](Cl)(=[O:20])=[O:19]>O>[CH3:17][S:18]([O:13][C:7]1[C:6](=[O:14])[C:5]2[C:10](=[CH:11][CH:2]=[CH:3][CH:4]=2)[N:9]([CH3:12])[CH:8]=1)(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 31297Methanesulfonyl chlorideHCID 231281077-Fluoro-3-hydroxy-1-methyl-4quinolone

Product 1

HCID 54314615Methyl-4-oxo-1,4-dihydroquinol-3-yl methanesulphonate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

7-Fluoro-3-hydroxy-1 -methyl-4-quinolone (4.5 g) was added to a solution of sodium hydroxide (12 g) in water (56 ml) and the mixture stirred at 0 to 5° with ice/water cooling. Methanesulphonyl chloride (4 ml) was added over a period of 1 5 minutes followed by aqueous sodium hydroxide (5M, 3 ml). The resultant solid was collected by filtration, washed with water (2×20 ml), and crystallised from industrial methylated spirit (220 ml) to give the novel compound 7-fluoro-]-methyl-4-oxo-1,4-dihydroquinol-3-yl methanesulphonate, m.p. 212°-213°.

Workup

  1. filtrationThe resultant solid was collected by filtration
  2. washwashed with water (2×20 ml)
  3. customcrystallised from industrial methylated spirit (220 ml)

Sources & evidence

ORD record
ord-ccaffaebd2e540f69214247be28a7ab6
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

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