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

HRID 1387404Notes

Reaction equation

HRID 1387404 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].C(O)(=O)C>[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

4

Reactant 1

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

Product 1

HCID 179825555-(Aminomethyl)indolin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A slurry of 5-cyanooxindole (1.0 g, 6.3 mmol) and 10 palladium on carbon (0.05 g) in glacial acetic acid (50 mL) at room temperature was hydrogenated under 40 psi pressure for 24 hours. The catalyst was removed by filtration through a pad of diatomaceous earth and the solvent evaporated from the filtrate to leave an orange oil of 5-aminomethyloxindole as an acetate salt (1.16 g). 1H NMR (DMSO-d6) δ7.21 (s, 1H), 7.14 (d, 1H, J=7.6 Hz), 6.75 (d, 1H, J=7.6 Hz), 3.74 (s, 2H), 3.44 (s, 2H). MS (+ve ES) 146 (100), (M−NH2).

Workup

  1. customThe catalyst was removed by filtration through a pad of diatomaceous earth
  2. customthe solvent evaporated from the filtrate

Sources & evidence

ORD record
ord-aba2b0320e1942f79b127003231cbe7c
Source dataset
uspto-grants-2001_07
Patent number
US06268391B1

Reaction notes

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