Ethanol → 1-(4-aminobenzyl)-5,6-dimethyl-1H-benzimidazole

HRID 30698Notes

Reaction equation

HRID 30698 reaction equation
[CH3:1][C:2]1[C:20]([CH3:21])=[CH:19][C:5]2[N:6]([CH2:9][C:10]3[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=3)[CH:7]=[N:8][C:4]=2[CH:3]=1.C(O)C>[C].[Pd].O1CCCC1>[NH2:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][N:6]2[C:5]3[CH:19]=[C:20]([CH3:21])[C:2]([CH3:1])=[CH:3][C:4]=3[N:8]=[CH:7]2)=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 457243895,6-dimethyl-1-(4-nitrobenzyl)-1H-benzimidazole

Product 1

HCID 201170811-(4-aminobenzyl)-5,6-dimethyl-1H-benzimidazoleYield 84.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5,6-dimethyl-1-(4-nitrobenzyl)-1H-benzimidazole (2.5 g), 10% palladium carbon (300 mg), ethanol (150 ml) and tetrahydrofuran (150 ml) was stirred under a hydrogen atmosphere at room temperature for 4 hrs. Palladium carbon was removed from the reaction mixture by filtration, and the filtrate was concentrated. Recrystallization of the residue from ethyl acetate-methanol gave 1-(4-aminobenzyl)-5,6-dimethyl-1H-benzimidazole (1.88 g, 84%) as colorless prism crystals. melting point: 238-239° C.

Workup

  1. customPalladium carbon was removed from the reaction mixture by filtration
  2. concentrationthe filtrate was concentrated
  3. customRecrystallization of the residue from ethyl acetate-methanol

Sources & evidence

ORD record
ord-4ff617ed74c44e07838bcf60627e9ca5
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

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