Water → HCID 178505237, compound

HRID 358668Notes

Reaction equation

HRID 358668 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N+:5]([O-])=[CH:4][CH:3]=1.[CH3:13][S:14]([O:17]S(C)(=O)=O)(=[O:16])=[O:15].C(=O)([O-])[O-].[K+].[K+].O>ClCCl>[CH3:13][S:14]([O:17][C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[OH:1])=[CH:10][CH:9]=[CH:8][CH:7]=2)(=[O:16])=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 81560Methanesulfonic anhydrideHCID 178526267HCID 178526267, compound

Product 1

HCID 178505237HCID 178505237, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-hydroxyquinoline-1-oxide (1 g), methanesulphonic anhydride (2 g) and potassium carbonate (2 g) in dichloromethane (20 ml) was stirred at 0° for 4 hours. Water (20 ml) was added to the mixture and the dichloromethane layer separated. The aqueous layer was extracted with dichloromethane (2×60 ml). The combined dichloromethane layer and extracts were dried over magnesium sulphate and evaporated to give a gum which was purified by flash chromatography on a silica gel column eluted with dichloromethane:methanol (19:1) to give the novel compound 4-hydroxyquinol-3-yl methanesulphonate, m.p. 224°.

Workup

  1. customthe dichloromethane layer separated
  2. extractionThe aqueous layer was extracted with dichloromethane (2×60 ml)
  3. dry with materialThe combined dichloromethane layer and extracts were dried over magnesium sulphate
  4. customevaporated
  5. customto give a gum which
  6. customwas purified by flash chromatography on a silica gel column
  7. washeluted with dichloromethane:methanol (19:1)

Sources & evidence

ORD record
ord-099bc7e77302403a8601fa537c584d49
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

Loading…