7-Nitroindole → 7-Aminoindole

HRID 13692

Reaction equation

HRID 13692 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[CH:9]2)([O-])=O.C([O-])=O.[NH4+]>C(O)C.[Pd]>[NH:11]1[C:12]2[C:8](=[CH:7][CH:6]=[CH:5][C:4]=2[NH2:1])[CH:9]=[CH:10]1

Participants

5

Reactant 2

HCID 233967-NitroindoleHCID 2723923Ammonium formate

Product 1

HCID 1116347-AminoindoleYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Dissolve 7-nitroindole in ethanol and add ammonium formate (10 equivalents) and a catalytic amount of 10% palladium on carbon. Heat the mixture to reflux for 1 hr before cooling, filter through celite, and evaporate to provide the product as a purple solid (99%).

Workup

  1. temperatureHeat the mixture
  2. temperatureto reflux for 1 hr
  3. temperaturebefore cooling
  4. filtrationfilter through celite
  5. customevaporate

Sources & evidence

ORD record
ord-d66e2b89479b4a10883eee173cc6ba93
Source dataset
uspto-grants-2010_06
Patent number
US07728150B2

Linked notes

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