Methyl iodide → Methyl-4-oxo-1,4-dihydroquinol-3-yl methanesulphonate

HRID 358669Notes

Reaction equation

HRID 358669 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[CH:11][CH:10]=2)(=[O:4])=[O:3].[C:17](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O>[CH3:1][S:2]([O:5][C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH3:17])[CH:7]=1)(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178505237HCID 178505237, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-hydroxyquinol-3-yl methanesulphonate (0.48 g) and potassium carbonate (0.28 g) in dry dimethylformamide (20 ml) was stirred for 2 hours at ambient temperature. Methyl iodide (0.15 ml) was then added and the stirring at ambient temperature continued overnight. The solvent was removed under reduced pressure and the residue was triturated with water (10 ml). The resultant mixture was extracted extracts were evaporated to dryness. The residue was purified by flash chromatography on a silica gel column eluted with dichloromethane:methanol (39:1) followed by crystallisation from industrial methylated spirit (10 ml) to give the novel compound ]-methyl-4-oxo-1,4-dihydroquinol-3-yl methanesulphonate, m.p. 206°-208°.

Workup

  1. waitthe stirring at ambient temperature continued overnight
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was triturated with water (10 ml)
  4. extractionThe resultant mixture was extracted extracts
  5. customwere evaporated to dryness
  6. customThe residue was purified by flash chromatography on a silica gel column
  7. washeluted with dichloromethane:methanol (39:1)
  8. customfollowed by crystallisation from industrial methylated spirit (10 ml)

Sources & evidence

ORD record
ord-7e9b4ce939a4404aa7ff237249413c5d
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

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