Reaction #488447

Reaction equation

3-tert-butyl-6-nitro-1H-indole

→

3-tert-butyl-1H-indol-6-ylamine

Yield 77.5%

Solvents

ethanol

Conditions

Workup

1. 1
   FiltrationThe catalyst was filtered off
2. 2
   Concentrationthe filtrate was concentrated to dryness
3. 3
   OtherThe residue was purified by column chromatography on silica gel (Pet.Ether./EtOAc 4:1)

Procedure

A suspension of 3-tert-butyl-6-nitro-1H-indole (3.0 g, 13.7 mmol) and Raney Ni (0.5 g) in ethanol was stirred at room temperature under H2 (1 atm) for 3 h. The catalyst was filtered off and the filtrate was concentrated to dryness. The residue was purified by column chromatography on silica gel (Pet.Ether./EtOAc 4:1) to give 3-tert-butyl-1H-indol-6-ylamine (B-11) (2.0 g, 77.3%) as a gray solid. 1H NMR (CDCl3): δ 7.58 (m, 2H), 6.73 (d, J=1.2 Hz, 1H), 6.66 (s, 1H), 6.57 (dd, J=0.8, 8.6 Hz, 1H), 3.60 (br s, 2H), 1.42 (s, 9H).

Source