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

HRID 423752Notes

Reaction equation

HRID 423752 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 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 6-nitro-1H-indole-3-carbonitrile (4.6 g, 24.6 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 (Pet. Ether/EtOAc=3/1) to give 6-amino-1H-indole-3-carbonitrile (B-8) (1 g, 99%) as a pink powder. 1H NMR (DMSO-d6) δ 11.51 (s, 1 H), 7.84 (d,J=2.4 Hz, 1 H), 7.22 (d,J=8.4 Hz, 1 H), 6.62 (s, 1H), 6.56 (d,J=8.4 Hz, 1 H), 5.0 (s, 2H); ESI-MS 157.1 m/z (MH+).

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrate was concentrated
  3. customthe residue was purified by column chromatography (Pet. Ether/EtOAc=3/1)

Sources & evidence

ORD record
ord-a93d412d53824bafab8c0fea32fa82e1
Source dataset
uspto-grants-2012_01
Patent number
US08101767B2

Reaction notes

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