Methanol → 5-Amino-2-oxindole

HRID 1387417Notes

Reaction equation

HRID 1387417 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.CO.[H][H]>CCOC(C)=O.[Pd]>[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

6

Reactant 3

HCID 887MethanolHCID 2303665-Nitro-2-oxindoleHCID 178418361HCID 178418361, compound

Product 1

HCID 27732135-Amino-2-oxindoleYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.5 g (8.4 mmol) of 5-nitro-1,3-dihydro-indol-2-one, 150 mg of Pd/C 10%, and 50 ml MeOH in 100 ml of EtOAc was placed on Parr® hydrogenator and charged with 45 psi of Hydrogen gas. The mixture was shaken for 2 hrs. The mixture was filtered and the solvent was removed in vacuo to yield 5-amino 1,3-dihydro-indol-2-one (1.22 g, 98%): 1H NMR (DMSO-d6): δ3.27 (s, 2H), 4.6 (s, 2H), 6.34 (dd, J1=2 Hz, J2=8.1 Hz, 1H), 6.45 (m, 2H), 9.88 (s, 1 H). APCI-MS: m/z 147 (m−H)−.

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-12dee6b2531048699fe663cf7aa96453
Source dataset
uspto-grants-2001_07
Patent number
US06268391B1

Reaction notes

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