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

HRID 1847794Notes

Reaction equation

HRID 1847794 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].[H][H]>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

5

Reactant 2

HCID 574701962-(Tert-butyl)-6-nitro-1H-indoleHCID 178418361HCID 178418361, compound

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 Nickel (0.2 g). The mixture was hydrogenated under 1 atm of hydrogen at room temperature 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-amine (1.0 g, 89%). 1H NMR (300 MHz, 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); MS (ESI) ink (M+H+) 189.1.

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-627f67accb5043129b16e58a38141be2
Source dataset
uspto-grants-2015_02
Patent number
US08952049B2

Reaction notes

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