5-ethyl-6-nitro-1H-indole → 5-ethyl-1H-indol-6-ylamine

HRID 1847474Notes

Reaction equation

HRID 1847474 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[N+:12]([O-])=O)[NH:8][CH:7]=[CH:6]2)[CH3:2]>[Ni]>[CH2:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[NH2:12])[NH:8][CH:7]=[CH:6]2)[CH3:2]

Participants

3

Reactant 1

HCID 574702065-ethyl-6-nitro-1H-indole

Product 1

HCID 571146005-ethyl-1H-indol-6-ylamineYield 48%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

A suspension of 5-ethyl-6-nitro-1H-indole (1.9 g, 10 mmol) and Raney Nickel (1 g) was hydrogenated under H2 (1 atm) at room temperature for 2 h. The catalyst was filtered off and the filtrate was concentrated to dryness. The residue was purified by silica gel column to give 5-ethyl-1H-indol-6-amine (760 mg, 48% over two steps). 1H NMR (CDCl3) δ 7.90 (br s, 1H), 7.41 (s, 1H), 7.00 (s, 1H), 6.78 (s, 2H), 6.39 (s, 1H), 3.39 (br s, 2H), 2.63 (q, J=7.2 Hz, 2H), 1.29 (t, J=6.9 Hz, 3H); MS (ESI) m/e (M+H+) 161.1.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated to dryness
  3. customThe residue was purified by silica gel column

Sources & evidence

ORD record
ord-e198f94e0cbf444dabe2ba0736d1f2fe
Source dataset
uspto-grants-2015_02
Patent number
US08952050B2

Reaction notes

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