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

HRID 843994Notes

Reaction equation

HRID 843994 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:11]#[N:12])[CH:8]=2)[NH:3]1.[H][H]>CO.O=[Pt]=O>[NH2:12][CH2:11][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[NH:3][C:2](=[O:1])[CH2:10]2

Participants

5

Reactant 2

HCID 27733462-Oxo-2,3-dihydro-1H-indole-5-carbonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 179825555-(Aminomethyl)indolin-2-one

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-Oxo-2,3-dihydro-1H-indole-5-carbonitrile (1.3 g) in methanol (30 ml) was added 10% PtO2 (0.200 g). This was shaken under 44 psi hydrogen over night. The catalyst was removed by filtration, and the mixture was dried over Na2SO4. The solution was concentrated to give a yellow solid, (1.1 g). MW 162; MS (m/e) 162 (M+).

Workup

  1. customThe catalyst was removed by filtration
  2. dry with materialthe mixture was dried over Na2SO4
  3. concentrationThe solution was concentrated
  4. customto give a yellow solid, (1.1 g)

Sources & evidence

ORD record
ord-129323e9068c4cefafcbf5953450a106
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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