5-bromo-6-nitro-1H-indole → 5-Bromo-1H-indol-6-amine

HRID 2404690Notes

Reaction equation

HRID 2404690 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-])=O)[NH:7][CH:6]=[CH:5]2>C(O)C.[Ni]>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH2:11])[NH:7][CH:6]=[CH:5]2

Participants

4

Reactant 1

HCID 197443315-bromo-6-nitro-1H-indole

Product 1

HCID 247295015-Bromo-1H-indol-6-amineYield 30.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 5-bromo-6-nitro-1H-indole (7.5 g, 31.1 mmol) and Raney Ni (1 g) in ethanol was stirred 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 column chromatography on silica gel to give 5-bromo-1H-indol-6-ylamine (B-27) (2 g, 30%). 1H NMR (DMSO-d6) δ 10.6 (s, 1H), 7.49 (s, 1H), 6.79-7.02 (m, 1H), 6.79 (s, 1H), 6.14-6.16 (m, 1H), 4.81 (s, 2H).

Workup

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

Sources & evidence

ORD record
ord-ed6f9e02521d48ebb9bb952473042deb
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

Loading…