6-nitro-1H-indole-2-carbonitrile → 6-Amino-1H-indole-2-carbonitrile

HRID 2038001Notes

Reaction equation

HRID 2038001 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[C:9]([C:13]#[N:14])[NH:10]2)=[CH:6][CH:5]=1)([O-])=O>[Ni].CCO>[NH2:1][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[C:9]([C:13]#[N:14])[NH:10]2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 574701946-nitro-1H-indole-2-carbonitrile

Product 1

HCID 451170156-Amino-1H-indole-2-carbonitrileYield 49%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 6-nitro-1H-indole-2-carbonitrile (2.5 g, 13 mmol) and Raney Nickel (500 mg) in EtOH (50 mL) was stirred at room temperature under H2(1 atm) for 1 h. Raney Nickel was removed via filtration and the filtrate was evaporated under reduced pressure to give a residue, which was purified by column chromatography on silica get to give 6-amino-1H-indole-2-carbonitrile (1.0 g, 49%). NMR (DMSO-d6) δ 12.75(br s, 1 H), 7.82(d, J=8 Hz, 1 H), 7.57(s, 1H), 7.42(s, 1 H), 7.15(d, J=8 Hz, 1 H); MS (ESI) m/e (M+H+) 158.2.

Workup

  1. customRaney Nickel was removed via filtration
  2. customthe filtrate was evaporated under reduced pressure
  3. customto give a residue, which
  4. customwas purified by column chromatography on silica
  5. customget

Sources & evidence

ORD record
ord-714085e5bafd4dfe9bb2af4174555bf9
Source dataset
uspto-grants-2013_11
Patent number
US08575209B2

Reaction notes

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