1-Methyl-6-nitro-1H-indole → 1-methyl-1H-indol-6-amine

HRID 651760Notes

Reaction equation

HRID 651760 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-])=O)[CH:9]=2)[CH:4]=[CH:3]1>C(O)C.O1CCCC1.[Pd]>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH2:11])[CH:9]=2)[CH:4]=[CH:3]1

Participants

5

Reactant 1

HCID 106073591-Methyl-6-nitro-1H-indole

Product 1

HCID 105347991-methyl-1H-indol-6-amine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-methyl-6-nitro-1H-indole (5.0 g, 28.4 mmol) and 10% Pd/C(1.0 g) in ethanol (200 ml) and tetrahydrofuran (100 ml) was hydrogenated at atmospheric pressure for 14 hours. The reaction mixture was filtered and concentrated to give 1-methyl-6-amino-1H-indole after crystallization from ether/hexane (3.8 g, 80%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-43114244a0d84dc88471a1748567d7c5
Source dataset
uspto-grants-2001_08
Patent number
US06281356B1

Reaction notes

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