2-(Tert-butyl)-6-nitro-1H-indole → 2-(tert-Butyl)-1H-indol-6-amine

HRID 1727490Notes

Reaction equation

HRID 1727490 reaction equation
[C:1]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([N+:14]([O-])=O)[CH:8]=2)([CH3:4])([CH3:3])[CH3:2]>CO.[Ni]>[C:1]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([NH2:14])[CH:8]=2)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 574701962-(Tert-butyl)-6-nitro-1H-indole

Product 1

HCID 574701972-(tert-Butyl)-1H-indol-6-amineYield 89%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-tert-butyl-6-nitro-1H-indole (1.3 g, 6.0 mmol) in MeOH (10 mL) was added Raney Ni (0.2 g). The mixture was stirred at room temperature under H2 (1 atm) for 3 h. The reaction mixture was filtered and the filtrate was concentrated. The residue was washed with petroleum ether to give 2-tert-butyl-1H-indol-6-ylamine (B-6) (1.0 g, 89%). 1H NMR (DMSO-d6) δ 10.19 (s, 1H), 6.99 (d, J=8.1 Hz, 1H), 6.46 (s, 1H), 6.25 (dd, J=1.8, 8.1 Hz, 1H), 5.79 (d, J=1.8 Hz, 1H), 4.52 (s, 2H), 1.24 (s, 9H); ESI-MS 189.1 m/z (MH+).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. washThe residue was washed with petroleum ether

Sources & evidence

ORD record
ord-f99f66c9e00b4c8abe5d6da0b285ebec
Source dataset
uspto-grants-2009_02
Patent number
US07495103B2

Reaction notes

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