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

HRID 1908455Notes

Reaction equation

HRID 1908455 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-9fba35f3c527456fb8cdff788e775adf
Source dataset
uspto-grants-2013_12
Patent number
US08598181B2

Reaction notes

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