1-benzyl-2-nitro-1H-imidazole → 1-Benzyl-1H-imidazol-2-ylamine

HRID 1189880Notes

Reaction equation

HRID 1189880 reaction equation
[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[N+:13]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Ni].CO>[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[NH2:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 3311201-benzyl-2-nitro-1H-imidazole

Product 1

HCID 426145331-Benzyl-1H-imidazol-2-ylamineYield 171.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A suspension of 1-benzyl-2-nitro-1H-imidazole (Step 160.2) (410 mg, 1.16 mmol) and Raney nickel (40 mg) in MeOH (10 mL) was stirred for 3 h at rt, under a hydrogen atmosphere. The reaction mixture was filtered through a pad of celite and concentrated to afford 345 mg of the title compound as a brown solid: ESI-MS: 173.9 [M+H]+; tR=2.02 min (System 1).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-66f575e835b5401f97110f76513e4ed3
Source dataset
uspto-grants-2014_03
Patent number
US08674099B2

Reaction notes

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