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

HRID 1915244Notes

Reaction equation

HRID 1915244 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.[N+](C1C=CC=C2C=1C=C(C#N)N2)([O-])=O>CCO.[Ni]>[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

5

Reactant 2

HCID 143689034-nitro-1H-indole-2-carbonitrileHCID 574701946-nitro-1H-indole-2-carbonitrile

Product 1

HCID 451170156-Amino-1H-indole-2-carbonitrile

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 6-nitro-1H-indole-2-carbonitrile and 4-nitro-1H-indole-2-carbonitrile (2.5 g, 13.4 mmol) and Raney Ni (500 mg) in EtOH (50 mL) was stirred at room temperature under H2 (1 atm) for 1 h. Raney Ni was filtered off. The filtrate was evaporated under reduced pressure and purified by column chromatography to give 6-amino-1H-indole-2-carbonitrile (B-5) (1 g, 49%). 1H NMR (DMSO-d6) δ 12.75 (br s, 1H), 7.82 (d, J=8 Hz, 1H), 7.57 (s, 1H), 7.42 (s, 1H), 7.15 (d, J=8 Hz, 1H); ESI-MS 158.2 m/z (MH+).

Workup

  1. filtrationRaney Ni was filtered off
  2. customThe filtrate was evaporated under reduced pressure
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-79af7e3051c0427baa952acd8d2f6537
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

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