(E)-2-(5-fluoro-2,4-dinitrophenyl)-N,N-dimethylethenamine → 5-Fluoro-1H-indol-6-amine

HRID 2038024Notes

Reaction equation

HRID 2038024 reaction equation
[F:1][C:2]1[C:3]([N+:16]([O-])=O)=[CH:4][C:5]([N+:13]([O-])=O)=[C:6](/[CH:8]=[CH:9]/N(C)C)[CH:7]=1>[Ni].CCO>[F:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][C:3]=1[NH2:16])[NH:13][CH:9]=[CH:8]2

Participants

4

Reactant 1

HCID 15022335(E)-2-(5-fluoro-2,4-dinitrophenyl)-N,N-dimethylethenamine

Product 1

HCID 150223365-Fluoro-1H-indol-6-amineYield 21.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A suspension of (E)-2-(5-fluoro-2,4-dinitrophenyl)-N,N-dimethylethenamine (8.0 g, 31 mmol) and Raney Nickel (8 g) in EtOH (80 mL) was stirred under H2(40 psi) at room temperature for 1 h. After filtration, the filtrate was concentrated and the residue was purified by column chromatography (petroleum ether/ethyl acetate=5/1) to give 5-fluoro-1H-indol-6-amine (1.0 g, 16%) as a brown solid. 1 HNMR (DMSO-d6) δ 10.56(br s, 1 H), 7.07(d, J=12 Hz, 1 H), 7.02(m, 1H), 6.71(d, J=8 Hz, 1H), 6.17(s, 1H), 3.91(br s 2H); MS (ESI) m/e (M+H+) 150.1.

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrate was concentrated
  3. customthe residue was purified by column chromatography (petroleum ether/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-2693ea9f6b384bb3a67efa46e8dbfdf2
Source dataset
uspto-grants-2013_11
Patent number
US08575209B2

Reaction notes

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