Dimethyl Sulfate → 1-Methyl-4-oxo-7-trifluoromethyl-1,4-dihydroquinol-3-yl methanesulphonate

HRID 358697Notes

Reaction equation

HRID 358697 reaction equation
S(OC)(O[CH3:5])(=O)=O.[CH3:8][S:9]([O:12][C:13]1[CH:14]=[N:15][C:16]2[C:21]([C:22]=1[OH:23])=[CH:20][CH:19]=[C:18]([C:24]([F:27])([F:26])[F:25])[CH:17]=2)(=[O:11])=[O:10].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH3:8][S:9]([O:12][C:13]1[C:22](=[O:23])[C:21]2[C:16](=[CH:17][C:18]([C:24]([F:27])([F:25])[F:26])=[CH:19][CH:20]=2)[N:15]([CH3:5])[CH:14]=1)(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 178505238HCID 178505238, compound

Product 1

HCID 541464311-Methyl-4-oxo-7-trifluoromethyl-1,4-dihydroquinol-3-yl methanesulphonate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Dimethyl sulphate (26.1ml) was added to a stirred suspension of 4-hydroxy-7-trifluoromethylquinol-3-yl methanesulphonate (7.19 g) and potassium carbonate (75.5 g) in dry 2-butanone (350 ml) and the resultant mixture was heated under reflux for 5 hours. The solvent was removed by distillation and the resultant residue was extracted with dichloromethane (600 ml then 400 ml). The combined extracts were dried over magnesium sulphate and the solvent was removed by distillation. The residue was purified by flash chromatography on a silica gel column eluted with dichloromethane:methanol (75:1) followed by flash chromatography on a silica gel column eluted with ethyl acetate and crystallisation from industrial methylated spirit (150 ml) to give the novel compound 1-methyl-4-oxo-7-trifluoromethyl-1,4-dihydroquinol-3-yl methanesulphonate, m.p. 218°.

Workup

  1. temperatureunder reflux for 5 hours
  2. customThe solvent was removed by distillation
  3. extractionthe resultant residue was extracted with dichloromethane (600 ml
  4. dry with materialThe combined extracts were dried over magnesium sulphate
  5. customthe solvent was removed by distillation
  6. customThe residue was purified by flash chromatography on a silica gel column
  7. washeluted with dichloromethane:methanol (75:1)
  8. washeluted with ethyl acetate and crystallisation from industrial methylated spirit (150 ml)

Sources & evidence

ORD record
ord-9ef236dbde934a57b7993e9f2b40f30f
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

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