HCID 86699717, compound → 4-Aminoindolin-2-one

HRID 1844101Notes

Reaction equation

HRID 1844101 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4](SC)[C:5](=[O:11])[NH:6]2>C(O)C.[Ni]>[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][C:5](=[O:11])[NH:6]2

Participants

4

Reactant 1

HCID 86699717HCID 86699717, compound

Product 1

HCID 122374724-Aminoindolin-2-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Under N2, compound D2 (0.8 g) was dissolved in ethanol (10 mL), treated with an excess of Raney nickel. The suspension was refluxed for 2 h. Analysis (TLC) showed the reaction completeness. The mixture was filtered through Celite and concentrated to give crude title compound D3. YD: 39.35%. 1H NMR (DMSO-d6) 400 MHz, δ: 3.152 (s, 2H), 5.011 (s, 2H), 6.052 (d, J=7.6 Hz, 1H), 6.211 (d, J=8.0, 1H), 6.831 (dd, J=7.6 & 8.0 Hz, 1H), 10.088 (s, 1H). MS (ESI): m/z 146.8 [M−H]−.

Workup

  1. temperatureThe suspension was refluxed for 2 h
  2. filtrationThe mixture was filtered through Celite
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-32a3db4771294c7783c3ba6cc21c699c
Source dataset
uspto-grants-2015_02
Patent number
US08946282B2

Reaction notes

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