4-Nitro-1,3-dihydro-2H-indol-2-one → 4-Aminoindolin-2-one

HRID 1275664Notes

Reaction equation

HRID 1275664 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][C:7](=[O:13])[NH:8]2)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][C:7](=[O:13])[NH:8]2

Participants

4

Reactant 1

HCID 216778744-Nitro-1,3-dihydro-2H-indol-2-one

Product 1

HCID 122374724-Aminoindolin-2-oneYield 76%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A catalytic amount of 10% palladium-on-carbon is added to a solution of 4-nitrooxindole (0.889 g, 4.99 mmol) in methanol (100 mL). The suspension is degassed three times and placed under an atmosphere of hydrogen for 3 hours. The suspension is filtered through a pad of Celite and the Celite is washed several times with methanol. The methanol from the filtrate is removed by rotary evaporation. The resulting residue is purified via silica gel column chromatography using 3% methanol/methylene chloride as the eluent. The appropriate fractions are combined and the solvents removed by rotary evaporation to yield 0.558 g of 4-aminooxindole as a light orange solid (76%).

Workup

  1. customThe suspension is degassed three times
  2. filtrationThe suspension is filtered through a pad of Celite
  3. washthe Celite is washed several times with methanol
  4. customThe methanol from the filtrate is removed by rotary evaporation
  5. customThe resulting residue is purified via silica gel column chromatography
  6. customthe solvents removed by rotary evaporation

Sources & evidence

ORD record
ord-8f12cb5d5bc64dd8a0f17997aeb65b51
Source dataset
uspto-grants-2000_12
Patent number
US06162818

Reaction notes

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