2-tert-Butyl-1-methyl-5-nitro-1H-indole → 2-(1,1-Dimethylethyl)-1-methyl-1H-indol-5-amine

HRID 1403899Notes

Reaction equation

HRID 1403899 reaction equation
[C:1]([C:5]1[N:6]([CH3:17])[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([N+:14]([O-])=O)=[CH:9][CH:8]=2)([CH3:4])([CH3:3])[CH3:2]>CO.[Ni]>[C:1]([C:5]1[N:6]([CH3:17])[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([NH2:14])=[CH:9][CH:8]=2)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 534211822-tert-Butyl-1-methyl-5-nitro-1H-indole

Product 1

HCID 591293302-(1,1-Dimethylethyl)-1-methyl-1H-indol-5-amineYield 66%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-tert-butyl-1-methyl-5-nitro-1H-indole (3.00 g, 13.7 mmol) in MeOH (30 mL) was added Raney Ni (0.3 g) under nitrogen atmosphere. The mixture was stirred under hydrogen atmosphere (1 atm) at room temperature overnight. The mixture was filtered through a Celite pad and the filtrate was evaporated under vacuum. The crude residue was purified by column chromatography on silica gel (P.E/EtOAc 20:1) to give 2-tert-butyl-1-methyl-1H-indol-5-amine (1.7 g, 66%). 1H NMR (300 MHz, CDCl3) δ 7.09 (d, J=8.4 Hz, 1H), 6.89-6.9 (m, 1H), 6.66 (dd, J=2.4, 8.7 Hz, 1H), 6.14 (d, J=0.6 Hz, 1H), 3.83 (s, 3H), 3.40 (brs, 2H), 1.45 (s, 9H); MS (ESI) m/e (M+H+) 203.1.

Workup

  1. filtrationThe mixture was filtered through a Celite pad
  2. customthe filtrate was evaporated under vacuum
  3. customThe crude residue was purified by column chromatography on silica gel (P.E/EtOAc 20:1)

Sources & evidence

ORD record
ord-0c4c57e9ccad434f9fc5fad6d5fc1c76
Source dataset
uspto-grants-2014_12
Patent number
US08912199B2

Reaction notes

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