Trifluoromethanesulfonic anhydride → Methyl 3-(((trifluoromethyl)sulfonyl)oxy)quinoline-8-carboxylate

HRID 472790Notes

Reaction equation

HRID 472790 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].O[C:17]1[CH:18]=[N:19][C:20]2[C:25]([CH:26]=1)=[CH:24][CH:23]=[CH:22][C:21]=2[C:27]([O:29][CH3:30])=[O:28].C([O-])(O)=O.[Na+]>N1C=CC=CC=1.C(Cl)Cl>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:17]1[CH:18]=[N:19][C:20]2[C:25]([CH:26]=1)=[CH:24][CH:23]=[CH:22][C:21]=2[C:27]([O:29][CH3:30])=[O:28])(=[O:5])=[O:4]

Participants

6

Reactant 3

HCID 67749Trifluoromethanesulfonic anhydride2×HCID 516892Sodium BicarbonateHCID 57440941Methyl 3-hydroxyquinoline-8-carboxylate

Product 1

HCID 58056975Methyl 3-(((trifluoromethyl)sulfonyl)oxy)quinoline-8-carboxylateYield 91%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

Trifluoromethanesulfonic anhydride (0.55 mL, 3.4 mmol) was added to a solution of methyl 3-hydroxyquinoline-8-carboxylate (650 mg, 3.2 mmol) in pyridine (2.3 mL) and CH2Cl2 (13 mL) at 0° C. The reaction mixture was allowed to warm to room temperature. After 3 h, additional trifluoromethanesulfonic anhydride (0.55 mL, 3.4 mmol) was added and the reaction was stirred for an additional 18 h. Saturated aqueous NaHCO3 (20 mL) was added and the layers were separated. The aqueous phase was extracted with CH2Cl2 (3×). The combined organic phase was dried (MgSO4), filtered and concentrated in vacuo. The resulting residue was purified on silica gel eluting with CH2Cl2 to afford 971 mg (91%) of methyl 3-(((trifluoromethyl)sulfonyl)oxy)quinoline-8-carboxylate.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous phase was extracted with CH2Cl2 (3×)
  3. dry with materialThe combined organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified on silica gel eluting with CH2Cl2

Sources & evidence

ORD record
ord-4a8e6bba1a38401f95540a4a7f4a9cd5
Source dataset
uspto-grants-2014_01
Patent number
US08633220B2

Reaction notes

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