5-Nitro-2-oxindole → 5-Amino-2-oxindole

HRID 2213669Notes

Reaction equation

HRID 2213669 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH2:7]2)([O-])=O>[Pd].CO>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH2:7]2

Participants

4

Reactant 1

HCID 2303665-Nitro-2-oxindole

Product 1

HCID 27732135-Amino-2-oxindoleYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 5-nitroindolin-2-one (2.0 g, 11.13 mmol), and 10% palladium on carbon (500 mg) in methanol (100 mL) was hydrogenated for 2 hours under 45 psi. The reaction mixture was filtered through celite and the resulting cake was washed with methanol. The filtrate was concentrated to afford 5-aminoindolin-2-one as a tan-colored solid (1.6 g).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washthe resulting cake was washed with methanol
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-24e931ad631441ff8c6df05d2d5167ee
Source dataset
uspto-grants-2006_09
Patent number
US07105563B2

Reaction notes

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