Trifluoromethanesulfonic anhydride → 2-Phenyl-3-methyl-8-trifluoromethanesulfonyloxyquinoline

HRID 1167178Notes

Reaction equation

HRID 1167178 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[C:16]1([C:22]2[C:31]([CH3:32])=[CH:30][C:29]3[C:24](=[C:25](O)[CH:26]=[CH:27][CH:28]=3)[N:23]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>N1C=CC=CC=1>[C:16]1([C:22]2[C:31]([CH3:32])=[CH:30][C:29]3[C:24](=[C:25]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])[CH:26]=[CH:27][CH:28]=3)[N:23]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 22995923HCID 22995923, compound

Product 1

HCID 155214792-Phenyl-3-methyl-8-trifluoromethanesulfonyloxyquinolineYield 91.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

16.9 ml (110 mmol) of trifluoromethane-sulfonic anhydride are added dropwise, at 0° C., to a solution of 12.5 g (53 mmol) of 2-phenyl-3-methyl-8-hydroxyquinoline in 150 ml of pyridine. The reaction mixture is then stirred for 16 hours at ambient temperature. After evaporating the pyridine, the residue is taken up in 200 ml of water and 100 ml of ethyl acetate. The aqueous phase is extracted with 2×100 ml of ethyl acetate. The organic phases are combined, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue is purified by silica gel chromatography (eluent: ethyl acetate/cyclohexane 3/7) to give 17.8 g of 2-phenyl-3-methyl-8-trifluoromethanesulfonyloxyquinoline in the form of a beige solid; M.p.=85° C. (Yield: 91%)

Workup

  1. customAfter evaporating the pyridine
  2. extractionThe aqueous phase is extracted with 2×100 ml of ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue is purified by silica gel chromatography (eluent: ethyl acetate/cyclohexane 3/7)

Sources & evidence

ORD record
ord-7ebea47144b44f889c6618c9bf291805
Source dataset
uspto-grants-2003_09
Patent number
US06617336B1

Reaction notes

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