6-Nitro-1H-indole-3-carbonitrile → 6-amino-1H-indole-3-carbonitrile

HRID 1847788Notes

Reaction equation

HRID 1847788 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:13]#[N:14])=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-])=O>CCO.[Pd]>[NH2:1][C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:13]#[N:14])=[CH:9][NH:10]2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 2831796-Nitro-1H-indole-3-carbonitrile

Product 1

HCID 444104646-amino-1H-indole-3-carbonitrileYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspention of 6-nitro-1H-indole-3-carbonitrile (4.6 g, 25 mmol) and 10% Pd—C (0.46 g) in EtOH (50 mL) was stirred under H2 (1 atm) at room temperature overnight. After filtration, the filtrate was concentrated and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=3/1) to give 6-amino-1H-indole-3-carbonitrile (1.0 g, 98%) as a pink solid. 1H NMR (DMSO-d6) δ 11.51 (s, 1H), 7.84 (d, J=2.4 Hz, 1H), 7.22 (d, J=8.4 Hz, 1H), 6.62 (s, 1H), 6.56 (d, J=8.4 Hz, 1H), 5.0 (s, 2H); MS (ESI) m/e (M+H+) 157.1.

Workup

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

Sources & evidence

ORD record
ord-acccd3d317474e2bb1371d3b8dde8504
Source dataset
uspto-grants-2015_02
Patent number
US08952049B2

Reaction notes

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