Ethanol → 5-amino-7-chloro-1,3-dihydro-2H-indol-2-one

HRID 1039100Notes

Reaction equation

HRID 1039100 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:12]([O-])=O)[CH:5]=[C:6]2[C:10]=1[NH:9][C:8](=[O:11])[CH2:7]2.CCO>[Pd].CCOC(C)=O>[NH2:12][C:4]1[CH:5]=[C:6]2[C:10](=[C:2]([Cl:1])[CH:3]=1)[NH:9][C:8](=[O:11])[CH2:7]2

Participants

5

Reactant 2

HCID 702EthanolHCID 66927316HCID 66927316, compound

Product 1

HCID 669271295-amino-7-chloro-1,3-dihydro-2H-indol-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

7-chloro-5-nitro-1,3-dihydro-2H-indol-2-one (6.1 g, 28.7 mmol) from Step 1 of this example was dissolved with stirring in 1:1 EtOH and EtOAc (287 ml). Palladium on carbon (10%, 1.8 g) was added and the slurry degassed, placed under an atmosphere of hydrogen (3×) and stirred at RT for 3 hours. The mixture was filtered through CELITE, the filter cake washed with EtOAc (3×100 ml), the filtrates combined and the volatiles removed in vacuum to give the titled compound.

Workup

  1. customthe slurry degassed
  2. filtrationThe mixture was filtered through CELITE
  3. washthe filter cake washed with EtOAc (3×100 ml)
  4. customthe volatiles removed in vacuum

Sources & evidence

ORD record
ord-fab984f5e22c47f6b3e68571b360f8bc
Source dataset
uspto-grants-2013_10
Patent number
US08552022B2

Reaction notes

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