2-Oxo-2,3-dihydro-1H-indole-5-carbonitrile → 5-(Aminomethyl)indolin-2-one

HRID 2213668Notes

Reaction equation

HRID 2213668 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6]2)#[N:2]>[Pd]>[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6]2

Participants

3

Reactant 1

HCID 27733462-Oxo-2,3-dihydro-1H-indole-5-carbonitrile

Product 1

HCID 179825555-(Aminomethyl)indolin-2-oneYield 107.2%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A slurry of 5-cyanoindolin-2-one (5 g, 31.64 mmol) and 10% palladium on carbon (500 mg), was hydrogenated under 40 psi at ambient temperature temp. for 24 hours. Filtration through a pad of celite and concentration afforded 5-aminomethylindolin-2-one (5.5 g) as an orange oil.

Workup

  1. customwas hydrogenated under 40 psi at ambient temperature
  2. filtrationFiltration
  3. concentrationthrough a pad of celite and concentration

Sources & evidence

ORD record
ord-cd3537787a68435a86cb5a7152035f46
Source dataset
uspto-grants-2006_09
Patent number
US07105563B2

Reaction notes

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