Pyridine → 2-Oxo-1,2,3,4-tetrahydro-5-quinolinyl trifluoromethanesulfonate

HRID 1811398Notes

Reaction equation

HRID 1811398 reaction equation
N1C=CC=CC=1.[F:7][C:8]([F:21])([F:20])[S:9]([O:12]S(C(F)(F)F)(=O)=O)(=[O:11])=[O:10].O[C:23]1[CH:32]=[CH:31][CH:30]=[C:29]2[C:24]=1[CH2:25][CH2:26][C:27](=[O:33])[NH:28]2>ClCCl>[F:7][C:8]([F:21])([F:20])[S:9]([O:12][C:23]1[CH:32]=[CH:31][CH:30]=[C:29]2[C:24]=1[CH2:25][CH2:26][C:27](=[O:33])[NH:28]2)(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 1691533,4-Dihydro-5-hydroxy-2(1H)-quinolinone

Product 1

HCID 533634512-Oxo-1,2,3,4-tetrahydro-5-quinolinyl trifluoromethanesulfonateYield 107%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine (30 ml) and trifluoromethanesulfonic anhydride (25 g) were added with stirring at 0° C. to an anhydrous dichloromethane solution (200 ml) of 5-hydroxy-3,4-dihydro-1H-quinolin-2-one (15.9 g), followed by stirring for 2 hours. The resulting mixture was concentrated under reduced pressure, water was added to the residue, and extraction with dichloromethane was performed. The extract was washed with water, an aqueous potassium hydrogensulfate solution and water in this order, and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the residue was recrystallized from an ethyl acetate-diisopropyl ether mixed solvent to thereby obtain 28 g (yield: 97%) of 5-trifluoromethanesulfonyloxy-3,4-dihydro-1H-quinolin-2-one as a light brown powder.

Workup

  1. concentrationThe resulting mixture was concentrated under reduced pressure, water
  2. additionwas added to the residue, and extraction with dichloromethane
  3. washThe extract was washed with water
  4. dry with materialan aqueous potassium hydrogensulfate solution and water in this order, and dried over anhydrous sodium sulfate
  5. concentrationAfter concentration under reduced pressure
  6. customthe residue was recrystallized from an ethyl acetate-diisopropyl ether mixed solvent

Sources & evidence

ORD record
ord-1f52fc1025854043b4616f8b5379415b
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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