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

HRID 1847769Notes

Reaction equation

HRID 1847769 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-efe5a7e0e43a455198021650c842c922
Source dataset
uspto-grants-2015_02
Patent number
US08952049B2

Reaction notes

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