Acetic Acid → 6-Amino-3,3-bis-trifluoromethyl-1,3-dihydro-indol-2-one

HRID 887603Notes

Reaction equation

HRID 887603 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:17]([F:20])([F:19])[F:18])([C:13]([F:16])([F:15])[F:14])[C:7](=[O:12])[N:8]2O)=[CH:4][CH:3]=1.CC(O)=O>C1COCC1.[Zn]>[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:13]([F:16])([F:14])[F:15])([C:17]([F:18])([F:19])[F:20])[C:7](=[O:12])[NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 219614506-Amino-1-hydroxy-3,3-bis-trifluoromethyl-1,3-dihydro-indol-2-one

Product 1

HCID 866307786-Amino-3,3-bis-trifluoromethyl-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.245 g (4.151 mmol) 6-amino-1-hydroxy-3,3-bis-trifluoromethyl-1,3-dihydro-indol-2-one in 80 ml THF was added 3.565 ml (62.27 mmol) glacial AcOH and 19 g (290.6 mmol) Zinc dust (100 mesh). The reaction was stirred 40 min at RT and then 5 h at reflux. The reaction was cooled to RT. The solvent was decanted and concentrated, then dissolved in EtOAc and filtered through Celite®. The EtOAc solution was then washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated and dried under vacuum, to yield the titled compound, as a yellow solid.

Workup

  1. temperature5 h at reflux
  2. temperatureThe reaction was cooled to RT
  3. customThe solvent was decanted
  4. concentrationconcentrated
  5. dissolutiondissolved in EtOAc
  6. filtrationfiltered through Celite®
  7. washThe EtOAc solution was then washed with saturated aqueous NaHCO3 and brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customdried under vacuum

Sources & evidence

ORD record
ord-c5c711786f1d44feb81a692a333a56b9
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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