Potassium Carbonate → HCID 178505239, compound

HRID 358715Notes

Reaction equation

HRID 358715 reaction equation
[CH3:1][S:2]([O:5]S(C)(=O)=O)(=[O:4])=[O:3].[OH:10][C:11]1[C:20]2[C:15](=[CH:16][C:17]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:18][CH:19]=2)[N+:14]([O-])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[CH3:1][S:2]([O:5][C:12]1[CH:13]=[N:14][C:15]2[C:20]([C:11]=1[OH:10])=[CH:19][CH:18]=[C:17]([O:21][C:22]([F:24])([F:25])[F:23])[CH:16]=2)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 81560Methanesulfonic anhydrideHCID 178526269HCID 178526269, compound

Product 1

HCID 178505239HCID 178505239, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulphonic anhydride (1.55 g) was added to a stirred mixture of 4-hydroxy-7-trifluoromethoxy-quinoline-1-oxide (2.0 g), potassium carbonate (1.2 g) and dichloromethane (100 ml) at 0°. After stirring at 0° for a further 2.5 hours, the reaction mixture was washed with saturated aqueous sodium carbonate (60 ml) and the dichloromethane phase separated. The aqueous phase was extracted with dichloromethane (2×50 ml) and the combined dichloromethane phase and extracts were dried over magnesium sulphate. The solvent was removed by evaporation and water (100 ml) followed by saturated aqueous sodium bicarbonate (5 ml) at 10° was added. The solid was collected by filtration to give the novel compound 4-hydroxy-7-trifluoromethoxyquinol-3-yl methanesulphonate, m.p. 125°-127°.

Workup

  1. washthe reaction mixture was washed with saturated aqueous sodium carbonate (60 ml)
  2. customthe dichloromethane phase separated
  3. extractionThe aqueous phase was extracted with dichloromethane (2×50 ml)
  4. dry with materialthe combined dichloromethane phase and extracts were dried over magnesium sulphate
  5. customThe solvent was removed by evaporation and water (100 ml)
  6. customfollowed by saturated aqueous sodium bicarbonate (5 ml) at 10°
  7. additionwas added
  8. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-b97f082efcd8485d99345e29eff241a8
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

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