Perchloric Acid → 1,3-Dihydro-1-(2,2,2-trifluoroethyl)-2H-indol-2-one

HRID 610077Notes

Reaction equation

HRID 610077 reaction equation
[F:1][C:2]([F:16])([F:15])[CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=O)[C:5]1=[O:14].Cl(O)(=O)(=O)=O>[Pd].C(O)(=O)C>[F:16][C:2]([F:1])([F:15])[CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][C:5]1=[O:14]

Participants

5

Reactant 2

HCID 24247Perchloric AcidHCID 19600971HCID 19600971, compound

Product 1

HCID 196009761,3-Dihydro-1-(2,2,2-trifluoroethyl)-2H-indol-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 1-(2,2,2-trifluoro-ethyl)-1H-indole-2,3-dione (9.2 g, 40 mmol) and 10% palladium on carbon (2.4 g) in acetic acid (100 mL) and 70% perchloric acid (6.4 mL, 80 mmol) was hydrogenated in a Parr apparatus for 22 hours. The mixture was filtered through diatomaceous earth, diluted with water (1.5 L) and the precipitate was collected and dried. mp 155-162° C. Yield 7.5 g (87%).

Workup

  1. filtrationThe mixture was filtered through diatomaceous earth
  2. additiondiluted with water (1.5 L)
  3. customthe precipitate was collected
  4. customdried

Sources & evidence

ORD record
ord-71726128dbff49b89aca16c8a8f66f7a
Source dataset
uspto-grants-1999_12
Patent number
US05998463

Reaction notes

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