5-Nitro-2-phenyl-1H-indole → 2-phenyl-1H-indol-5-amine

HRID 1991703Notes

Reaction equation

HRID 1991703 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:7]2)([O-])=O>CO.[Ni]>[C:13]1([C:8]2[NH:9][C:10]3[C:6]([CH:7]=2)=[CH:5][C:4]([NH2:1])=[CH:12][CH:11]=3)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 1

HCID 2803095-Nitro-2-phenyl-1H-indole

Product 1

HCID 98371822-phenyl-1H-indol-5-amineYield 77%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5-nitro-2-phenyl-1H-indole (2.83 g, 0.01 mol) in MeOH (30 mL) was added Raney Ni (510 mg) under nitrogen atmosphere. The mixture was stirred under hydrogen atmosphere (1 atm) at room temperature overnight. The catalyst was filtered through a Celite pad and the filtrate was evaporated under vacuum to give the crude product, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=5/1) to give 2-phenyl-1H-indol-5-amine (1.6 g, 77%). 1H NMR (400 MHz, CDCl3) δ 7.76 (d, J=7.6 Hz, 2H), 7.39 (t, J=7.6 Hz, 2H), 7.24 (t, J=7.6 Hz, 1H), 7.07 (d, J=8.4 Hz, 1H), 6.64 (d, J=1.6 Hz, 1H), 6.60 (d, J=1.2 Hz, 1H), 6.48 (dd, J=2.0, 8.4 Hz, 1H), 4.48 (brs, 2H); MS (ESI) m/e (M+H+) 209.0.

Workup

  1. filtrationThe catalyst was filtered through a Celite pad
  2. customthe filtrate was evaporated under vacuum
  3. customto give the crude product, which
  4. customwas purified by column chromatography on silica gel (petroleum ether/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-90e48fc35a61477eb19fb3916699db61
Source dataset
uspto-grants-2010_01
Patent number
US07645789B2

Reaction notes

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