Water → HCID 178505236, compound

HRID 358718Notes

Reaction equation

HRID 358718 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]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:18][CH:19]=2)[N+:14]([O-])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].O>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]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH:16]=2)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 81560Methanesulfonic anhydrideHCID 178526266HCID 178526266, compound

Product 1

HCID 178505236HCID 178505236, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methanesulphonic anhydride (3.05 g) in dichloromethane (10 ml) was added to a mixture of 4-hydroxy-7-phenylquinoline-1-oxide (3.28 g), potassium carbonate (2.13 g) and dichloromethane (160 ml) at 0°, the mixture was stirred at 0° for 2 hours, then allowed to warm to room temperature. Water (250 ml) was added, the layers were separated and the aqueous layer was extracted with dichloromethane (3×100 ml). The combined dichloromethane layer and extracts were dried over magnesium sulphate and the solvent was removed by distillation. The residue was subjected to flash chromatography on two successive silica gel columns eluted with dichloromethane: industrial methylated spirit (19:1) to give crude 4-hydroxy-7-phenylquinol-3-yl methanesulphonate.

Workup

  1. customthe layers were separated
  2. extractionthe aqueous layer was extracted with dichloromethane (3×100 ml)
  3. dry with materialThe combined dichloromethane layer and extracts were dried over magnesium sulphate
  4. customthe solvent was removed by distillation
  5. washeluted with dichloromethane: industrial methylated spirit (19:1)

Sources & evidence

ORD record
ord-3d8671c46a014794a487186a325100c7
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

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