5-Fluoro-7-nitro-1,3-dihydro-indol-2-one → 7-Amino-5-fluoroindolin-2-one

HRID 2191435Notes

Reaction equation

HRID 2191435 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([N+:11]([O-])=O)[CH:10]=1)[NH:7][C:6](=[O:14])[CH2:5]2>C(O)(=O)C.[Pd]>[NH2:11][C:9]1[CH:10]=[C:2]([F:1])[CH:3]=[C:4]2[C:8]=1[NH:7][C:6](=[O:14])[CH2:5]2

Participants

4

Reactant 1

HCID 592500625-Fluoro-7-nitro-1,3-dihydro-indol-2-one

Product 1

HCID 592500547-Amino-5-fluoroindolin-2-oneYield 97.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

5-Fluoro-7-nitro-1,3-dihydro-indol-2-one 20a (4.0 g, 20 mmol) was dissolved in 200 ml of acetic acid under stirring, and added with palladium on activated carbon (1.0 g, 5%) at room temperature. The reaction system was stirred under a hydrogen atmosphere. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was filtered, and concentrated under reduced pressure to obtain the title compound 7-amino-5-fluoro-1,3-dihydro-indol-2-one 20b (3.2 g, yield 97.5%) as a white solid.

Workup

  1. stirringThe reaction system was stirred under a hydrogen atmosphere
  2. filtrationthe reaction mixture was filtered
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b6f3c1022aa64b19a2fe88a4783c6c40
Source dataset
uspto-grants-2012_12
Patent number
US08329682B2

Reaction notes

Loading…