1h-Indole-3-acetonitrile, 6-nitro- → 2-(6-Amino-1h-indol-3-yl)acetonitrile

HRID 1915255Notes

Reaction equation

HRID 1915255 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([CH2:13][C:14]#[N:15])=[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]([CH2:13][C:14]#[N:15])=[CH:9][NH:10]2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 2523851h-Indole-3-acetonitrile, 6-nitro-

Product 1

HCID 513582822-(6-Amino-1h-indol-3-yl)acetonitrile

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of (6-nitro-1H-indol-3-yl)-acetonitrile (B-9-a) (1.5 g, 74.5 mL) and 10% Pd—C (300 mg) in EtOH (50 mL) was stirred at room temperature under H2 (1 atm) for 5 h. Pd—C was removed via filtration and the filtrate was evaporated to give (6-amino-1H-indol-3-yl)-acetonitrile (B-9) (1.1 g, 90%). 1H NMR (DMSO-d6) δ 10.4 (br s, 1H), 7.18 (d, J=8.4 Hz, 1H), 6.94 (s, 1H), 6.52 (s, 1H), 6.42 (dd, J=8.4, 1.8 Hz, 1H), 4.76 (s, 2H), 3.88 (s, 2H); ESI-MS 172.1 m/z (MH+).

Workup

  1. customPd—C was removed via filtration
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-2f5095d70710451381f568583ac48972
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

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