5-bromo-6-nitro-1H-indole → 5-Bromo-1H-indol-6-amine
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]2Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
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
- filtrationThe catalyst was filtered off
- concentrationthe filtrate was concentrated to dryness
- customThe residue was purified by column chromatography on silica gel
Sources & evidence
- ORD record
- ord-d00f7064833046eaa29484532d17f2d8
- Source dataset
- uspto-grants-2009_02
- Patent number
- US07495103B2
Reaction notes
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