Water → 4-{3,5-Bis(trifluoromethyl)phenyl}-2-quinolinone

HRID 2090541Notes

Reaction equation

HRID 2090541 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]([C:13](=O)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[NH2:20])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[C:24](OC(=O)C)(=[O:26])[CH3:25].CC(C)([O-])C.[K+].O>C1(C)C=CC=CC=1>[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]([C:13]2[C:14]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:20][C:24](=[O:26])[CH:25]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 23665647Potassium tert-butoxideHCID 866513633',5'-Bis(trifluoromethyl)-2-aminobenzophenone

Product 1

HCID 866513644-{3,5-Bis(trifluoromethyl)phenyl}-2-quinolinoneYield 32%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Further, in a nitrogen atmosphere, 3′,5′-bis(trifluoromethyl)-2-aminobenzophenone (1.1 g, 3.3 mmol) was dissolved in toluene (13 mL), and acetic anhydride (0.62 mL, 6.5 mL) was added to the solution at room temperature, followed by stirring while heating and refluxing. The mixture was cooled to room temperature and then concentrated using a rotary evaporator. The residue was dissolved in ethylene glycol dimethyl ether (13 mL), and potassium tert-butoxide (1.5 mL, 13 mmol) was added to the solution at room temperature, followed by stirring for 2 hours. Water was added to the reaction solution, followed by extraction with methylene chloride. The organic layer was dried and then concentrated using a rotary evaporator. The residue was purified by silica gel column chromatography (hexane/ethyl acetate). Thus, 4-{3,5-bis(trifluoromethyl)phenyl}-2-quinolinone (372 mg, 1.04 mmol) was obtained in a yield of 32%.

Workup

  1. temperaturewhile heating
  2. temperaturerefluxing
  3. concentrationconcentrated
  4. customa rotary evaporator
  5. dissolutionThe residue was dissolved in ethylene glycol dimethyl ether (13 mL)
  6. stirringby stirring for 2 hours
  7. extractionfollowed by extraction with methylene chloride
  8. customThe organic layer was dried
  9. concentrationconcentrated
  10. customa rotary evaporator
  11. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-719ba463cdfb48ce9406c753ab519ff3
Source dataset
uspto-grants-2013_05
Patent number
US08436173B2

Reaction notes

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