6-Hydroxyquinoline → 6-Quinolinyl trifluoromethanesulfonate

HRID 1890925Notes

Reaction equation

HRID 1890925 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([OH:11])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[O:12](S(C(F)(F)F)(=O)=O)[S:13]([C:16]([F:19])([F:18])[F:17])(=O)=[O:14]>N1C=CC=CC=1>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([O:11][S:13]([C:16]([F:19])([F:18])[F:17])(=[O:14])=[O:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 113746-HydroxyquinolineHCID 67749Trifluoromethanesulfonic anhydride

Product 1

HCID 152903586-Quinolinyl trifluoromethanesulfonateYield 70.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

Quinolin-6-ol (2.9 g, 20 mmol) was dissolved in pyridine (30 mL). The mixture was cooled to 0° C. in an ice bath under nitrogen and Tf2O (4 mL, 24 mmol) was added to the reaction mixture slowly. The reaction mixture was stirred at room temperature for 5 hours, before partitioning between dichloromethane (50 mL) and saturated aqueous NaHCO3 (50 mL). The organic phase was separated and washed with brine (5×30 mL). The organic phase was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography to give 3.9 g of trifluoromethanesulfonic acid quinolin-6-yl ester as a brown oil (70% yield).

Workup

  1. custombefore partitioning between dichloromethane (50 mL) and saturated aqueous NaHCO3 (50 mL)
  2. customThe organic phase was separated
  3. washwashed with brine (5×30 mL)
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-4bb6094a554c458e93c50cd0269b0d4f
Source dataset
uspto-grants-2013_08
Patent number
US08507489B2

Reaction notes

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