Methanesulfonyl chloride → Methyl-4-oxo-1,4-dihydroquinol-3-yl methanesulphonate

HRID 358657Notes

Reaction equation

HRID 358657 reaction equation
[OH:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH3:13])[CH:3]=1.[CH3:14][S:15](Cl)(=[O:17])=[O:16]>[OH-].[Na+].O>[CH3:14][S:15]([O:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH3:13])[CH:3]=1)(=[O:17])=[O:16]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 5900784(1H)-Quinolinone, 3-hydroxy-1-methyl-

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

3-Hydroxy-1-methyl-4-quinolone (30 g) was dissolved in a solution of sodium hydroxide (8 g) in water (440 ml). Activated carbon (3 g) was added and the mixture stirred at 40° for 15 minutes. The mixture was filtered and the filtrate cooled in an ice/salt bath at 0 to 5° under nitrogen. Methanesulphonyl chloride (1 5.5 ml) was added dropwise over 30 minutes and the mixture then stirred at 0 to 5° for 30 minutes. Aqueous sodium hydroxide (5M, 40 ml) was added and the mixture stirred at 0 to 5° for a further 90 minutes. The resultant solid was collected by filtration and washed with water (2×50 ml) to yield crude product. The filtrate was treated with further methanesulphonyl chloride (15.5 ml) in a similar manner to that described above to give a second crop of crude product. The two crops of crude product were combined and crystallised from industrial methylated spirit (2 1) to give the novel compound 1-methyl-4-oxo-1,4-dihydroquinol-3-yl methanesulphonate, m.p. 208°-209°.

Workup

  1. additionActivated carbon (3 g) was added
  2. filtrationThe mixture was filtered
  3. temperaturethe filtrate cooled in an ice/salt bath at 0 to 5° under nitrogen
  4. additionMethanesulphonyl chloride (1 5.5 ml) was added dropwise over 30 minutes
  5. stirringthe mixture then stirred at 0 to 5° for 30 minutes
  6. additionAqueous sodium hydroxide (5M, 40 ml) was added
  7. stirringthe mixture stirred at 0 to 5° for a further 90 minutes
  8. filtrationThe resultant solid was collected by filtration
  9. washwashed with water (2×50 ml)
  10. customto yield crude product
  11. customto give a second crop of crude product
  12. customcrystallised from industrial methylated spirit (2 1)

Sources & evidence

ORD record
ord-b59f7c30b1e548b485d5a9b5fa6a2169
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

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