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

HRID 1167189Notes

Reaction equation

HRID 1167189 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 99%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

6.4 ml (38 mmol) of trifluoromethanesulfonic anhydride are added dropwise, at 0° C., to a solution of 4.3 g (18.3 mmol) of 2-phenyl-3-methyl-8-hydroxyquinoline in 50 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 100 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 to give 6.6 g of 2-phenyl-3-methyl-8-trifluoromethanesulfonyloxyquinoline in the form of a beige solid; M.p.=85° C. (Yield: 99%)

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

Sources & evidence

ORD record
ord-e1be51bc212c4b9bac17a7b0047c2050
Source dataset
uspto-grants-2003_09
Patent number
US06617336B1

Reaction notes

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