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

HRID 1908497Notes

Reaction equation

HRID 1908497 reaction equation
[Cl: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>[Cl: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 59129321(E)-2-(5-chloro-2,4-dinitrophenyl)-N,N-dimethylethenamine

Product 1

HCID 571918395-Chloro-1H-indol-6-amineYield 16.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A suspension of (E)-2-(5-chloro-2,4-dinitrophenyl)-N,N-dimethylethenamine (9.8 g, 36 mmol) and Raney Nickel (9.8 g) in EtOH (140 mL) was stirred under H2 (1 atm) at room temperature for 4 h. After filtration, the filtrate was concentrated and the residue was purified by column chromatograph (petroleum ether/ethyl acetate=10:1) to give 5-chloro-1H-indol-6-amine (0.97 g, 16%) as a gray powder. 1HNMR (CDCl3) δ 7.85 (br s, 1H), 7.52 (s, 1H), 7.03 (s, 1H), 6.79 (s, 1H), 6.34 (s, 1H), 3.91 (br s, 1H); MS (ESI) m/e (M+H+) 166.0.

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrate was concentrated
  3. customthe residue was purified by column chromatograph (petroleum ether/ethyl acetate=10:1)

Sources & evidence

ORD record
ord-30914d051882463299077af7b601e9dd
Source dataset
uspto-grants-2013_12
Patent number
US08598181B2

Reaction notes

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