Water → HCID 178505238, compound

HRID 358696Notes

Reaction equation

HRID 358696 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:10]=2)[N+:5]([O-])=[CH:4][CH:3]=1.[CH3:17][S:18]([O:21]S(C)(=O)=O)(=[O:20])=[O:19].C(=O)([O-])[O-].[K+].[K+].O>ClCCl>[CH3:17][S:18]([O:21][C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[OH:1])=[CH:10][CH:9]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:7]=2)(=[O:20])=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium Carbonate2×HCID 81560Methanesulfonic anhydride2×HCID 178526268HCID 178526268, compound

Product 1

HCID 178505238HCID 178505238, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-hydroxy-7-trifluoromethyl-quinoline-1-oxide (2.0 g), methanesulphonic anhydride (1.7 g) and potassium carbonate (1.3 g) in dichloromethane (100 ml) was stirred at 0° for 2 hours. Further methanesulphonic anhydride (1.7 g) and potassium carbonate (1.3 g) were then added and the mixture was stirred at ambient temperature overnight. Water (50 ml) was added and the precipitated solid collected by filtration to give a first crop of the novel compound 4-hydroxy-7-trifluoromethylquinol-3-yl methanesulphonate, m.p. 220°. The dichloromethane layer of the filtrate was separated and the aqueous layer subsequently extracted with dichloromethane (2×25 ml). The combined dichloromethane layer and extracts were evaporated to dryness. The residue was purified by flash chromatography on a silica gel column eluted with dichloromethane:methanol (20:1) to give a second crop of 4-hydroxy-7-trifluoromethylquinol-3-yl methanesulphonate, m.p. 220°.

Workup

  1. stirringthe mixture was stirred at ambient temperature overnight
  2. filtrationthe precipitated solid collected by filtration

Sources & evidence

ORD record
ord-ca455c6553ee4e13a3085e592c9e8c62
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

Loading…