7-Methyl-5-nitro-1H-indole → 7-Methyl-1H-indol-5-amine

HRID 2300388Notes

Reaction equation

HRID 2300388 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N+:11]([O-])=O)[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2>CO.[Pd]>[CH3:1][C:2]1[CH:3]=[C:4]([NH2:11])[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2

Participants

4

Reactant 1

HCID 154534667-Methyl-5-nitro-1H-indole

Product 1

HCID 154345017-Methyl-1H-indol-5-amineYield 55%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 7-methyl-5-nitroindole (0.35 g, 2.0 mmol) and 10% Pd/C (50 mg) in 20 mL of MeOH was stirred under H2. The reaction mixture was filtered and concentrated in vacuo, yielding an oil (0.16 g, 1.1 mmol, 41%), which was characterized by NMR and subjected to the following reaction without further purification.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9cdf53323d05430f93492ccf333b53ea
Source dataset
uspto-grants-2002_12
Patent number
US06498177B2

Reaction notes

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