2-(1-Methylethyl)-5-nitro-1H-indole → HCID 59129404, compound

HRID 1991738Notes

Reaction equation

HRID 1991738 reaction equation
[CH:1]([C:4]1[NH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([N+:13]([O-])=O)=[CH:8][CH:7]=2)([CH3:3])[CH3:2]>[Ni].CO>[CH:1]([C:4]1[NH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([NH2:13])=[CH:8][CH:7]=2)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 107268712-(1-Methylethyl)-5-nitro-1H-indole

Product 1

HCID 59129404HCID 59129404, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A suspension of 2-isopropyl-5-nitro-1H-indole (100 mg, 0.49 mmol) and Raney Nickel (10 mg) in MeOH (10 mL) was hydrogenated under hydrogen (1 atm) at the room temperature overnight. The catalyst was filtered off through a celite pad and the filtrate was evaporated under vacuum to give a residue, which was purified by column (petroleum ether/ethyl acetate=5/1) to give 2-isopropyl-1H-indol-5-amine (35 mg, 41%). 1H NMR (400 MHz, CDCl3) δ 7.69 (br s, 1H), 7.10 (d, J=8.4 Hz, 1H), 6.86 (d, J=2.4 Hz, 1H), 6.58 (dd, J=2.4, 8.8 Hz, 1H), 6.07 (t, J=1.2 Hz, 1H), 3.55 (br s, 2H), 3.06-2.99 (m, 1H), 1.33 (d, J=7.2 Hz, 6H); MS (ESI) m/e (M+H+) 175.4.

Workup

  1. customwas hydrogenated under hydrogen (1 atm) at the room temperature overnight
  2. filtrationThe catalyst was filtered off through a celite pad
  3. customthe filtrate was evaporated under vacuum
  4. customto give a residue, which
  5. customwas purified by column (petroleum ether/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-fe72ad45d170441ebbf4f4e07105d313
Source dataset
uspto-grants-2010_01
Patent number
US07645789B2

Reaction notes

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