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

HRID 2038003Notes

Reaction equation

HRID 2038003 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 suspension 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, 1 H 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, 2 H); 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-a2204ed8ab26425aa191eb78aa1061b2
Source dataset
uspto-grants-2013_11
Patent number
US08575209B2

Reaction notes

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