Ethanol → 5-Amino-7-fluoroindolin-2-one

HRID 1039097Notes

Reaction equation

HRID 1039097 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:12]([O-])=O)[CH:5]=[C:6]2[C:10]=1[NH:9][C:8](=[O:11])[CH2:7]2.CCO>[Pd].CCOC(C)=O>[NH2:12][C:4]1[CH:5]=[C:6]2[C:10](=[C:2]([F:1])[CH:3]=1)[NH:9][C:8](=[O:11])[CH2:7]2

Participants

5

Reactant 2

HCID 702EthanolHCID 669271437-Fluoro-5-nitroindolin-2-one

Product 1

HCID 669270705-Amino-7-fluoroindolin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

7-fluoro-5-nitro-1,3-dihydro-2H-indol-2-one (8.5 g, 43.3 mmol) from Step 1 of this example was dissolved with stirring in 1:1 EtOH and EtOAc (433 ml). Palladium on carbon (10%, 2.55 g) was added and the slurry degassed and placed under an atmosphere of hydrogen (3×) and stirred at RT for 3 hours. The mixture was filtered through CELITE, the filter cake washed with EtOAc (3×100 ml), the filtrates combined and the volatiles removed in vacuum to give the titled compound.

Workup

  1. customthe slurry degassed
  2. filtrationThe mixture was filtered through CELITE
  3. washthe filter cake washed with EtOAc (3×100 ml)
  4. customthe volatiles removed in vacuum

Sources & evidence

ORD record
ord-2003b8e8e736494d989293efcaa1259e
Source dataset
uspto-grants-2013_10
Patent number
US08552022B2

Reaction notes

Loading…