4-Nitro-1H-indole → 4-Aminoindole

HRID 240468

Reaction equation

HRID 240468 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2)([O-])=O.[H][H]>[Pd].C1COCC1>[NH2:1][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2

Participants

5

Reactant 2

HCID 1457664-Nitro-1H-indoleHCID 178418361HCID 178418361, compound

Product 1

HCID 5834314-Aminoindole

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A round-bottom flask was charged with 4-nitroindole (4.8 g, 30 mmol), Palladium on carbon (10%, 480 mg), and THF (50 mL), and the mixture was stirred under one hydrogen atmosphere overnight. TLC showed the reaction was complete. The catalyst was filtered off and the filtrate was concentrated to afford 4-amino-1H-indole, which was used directly in the next step without purification.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-c9141032da62429ea72e176f8ff59e25
Source dataset
uspto-grants-2014_02
Patent number
US08648086B2

Linked notes

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