HCID 59129306, compound → 5-(Trifluoromethyl)-1H-indol-6-amine

HRID 1847467Notes

Reaction equation

HRID 1847467 reaction equation
[N+]([C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[C:7]([C:13]([F:16])([F:15])[F:14])=[CH:6][C:5]=1/[CH:17]=[CH:18]/[N:19](C)C)([O-])=O>[Ni].C(O)C>[F:16][C:13]([F:14])([F:15])[C:7]1[CH:6]=[C:5]2[C:4](=[CH:9][C:8]=1[NH2:10])[NH:19][CH:18]=[CH:17]2

Participants

4

Reactant 1

HCID 59129306HCID 59129306, compound

Product 1

HCID 574702045-(Trifluoromethyl)-1H-indol-6-amineYield 14.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A suspension of (E)-2-(2,4-dinitro-5-(trifluoromethyl)phenyl)-N,N-dimethylethenamine (2.1 g, 6.9 mmol) and Raney Nickel (1 g) in ethanol (80 mL) was stirred under H2 (1 atm) at room temperature for 5 h. The catalyst was filtered off and the filtrate was concentrated to dryness. The residue was purified by column on silica gel to give 5-(trifluoromethyl)-1H-indol-6-amine (200 mg, 14%). 1H NMR (DMSO-d6) δ 10.79 (br s, 1H), 7.55 (s, 1H), 7.12 (s, 1H), 6.78 (s, 1H), 6.27 (s, 1H), 4.92 (s, 2H); MS (ESI) m/e 200.8.

Workup

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

Sources & evidence

ORD record
ord-72709184d3b443be9a54ae44c8027dbb
Source dataset
uspto-grants-2015_02
Patent number
US08952050B2

Reaction notes

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