Trifluoromethanesulfonic anhydride → Quinolin-7-yl trifluoromethanesulfonate

HRID 736026Notes

Reaction equation

HRID 736026 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:26]=[C:25]2[C:20]([CH:21]=[CH:22][CH:23]=[N:24]2)=[CH:19][CH:18]=1>N1C=CC=CC=1>[O:6]([C:17]1[CH:26]=[C:25]2[C:20]([CH:21]=[CH:22][CH:23]=[N:24]2)=[CH:19][CH:18]=1)[S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4]

Participants

4

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 1354268667-Hydroxyquinoline

Product 1

HCID 59296115Quinolin-7-yl trifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Trifluoromethanesulfonic anhydride (28.5 mL) was added dropwise to a solution of 7-hydroxyquinoline (22.0 g) in anhydrous pyridine (100 mL) cooled on ice. After 10 minutes, the mixture was warmed to ambient temperature and stirred overnight. The mixture was poured into 1000 mL of ice-cold 1 N HCl and extracted three times with 500 mL of ether. The combined organic extracts were washed once with water and once with brine, then dried over MgSO4, filtered, and evaporated. The crude product was chromatographed on silica gel (1:1 ethyl acetate/hexanes), then crystallized from hot hexane, yielding 32.3 g of product as pale yellow crystals. 1H-NMR (CDCl3): δ 8.98 (1H, dd, J=1.6, 4.4 Hz), 8.21 (1H, d, J=7.6 Hz), 8.03 (1H, d, J=2.4 Hz), 7.91 (1H, d, J=8.8 Hz), 7.48 (2H, m). 13C-NMR (CDCl3): δ 151.4, 149.9, 146.9, 137.3, 130.4, 127.5, 122.3, 121.1, 120.2, 118.7 (q, JCF=320 Hz).

Workup

  1. temperaturecooled on ice
  2. extractionextracted three times with 500 mL of ether
  3. washThe combined organic extracts were washed once with water and once with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was chromatographed on silica gel (1:1 ethyl acetate/hexanes)
  8. customcrystallized from hot hexane

Sources & evidence

ORD record
ord-9c653a1d73724efda1b6ab5dbd3f887e
Source dataset
uspto-grants-2009_09
Patent number
US07595300B2

Reaction notes

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