HCID 85787464, compound → 4-Fluoroindole

HRID 880512Notes

Reaction equation

HRID 880512 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+]([O-])=O)[C:3]=1[CH:11]=[CH:12][N:13]1CCCC1>[Ni].CO>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[CH:11]=[CH:12][NH:13]2

Participants

4

Reactant 1

HCID 85787464HCID 85787464, compound

Product 1

HCID 27745024-FluoroindoleYield 60%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Raney Nickel (500 mg) was added to a suspension of 1-[2-(2-fluoro-6-nitro-phenyl)vinyl]pyrrolidine (6 g, 25.42 mmol) in methanol (50 mL) and hydrogenated under atmospheric pressure at ambient temperature for 20 h. The mixture was filtered through a pad of Celite and the filtrate was concentrated in vacuo to afford 4-fluoro-1H-indole (2.05 g, 60%) as a brown liquid.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-a6c39d484c534538829a96555ad6622f
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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