Ammonia → 3-(1H-Imidazol-1-yl)benzaldehyde

HRID 1645832Notes

Reaction equation

HRID 1645832 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[NH:10]1[CH:14]=[CH:13][N:12]=[CH:11]1.N>[Cu].O>[N:10]1([C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=2)[CH:5]=[O:6])[CH:14]=[CH:13][N:12]=[CH:11]1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 795ImidazoleHCID 765833-Bromobenzaldehyde

Product 1

HCID 156504083-(1H-Imidazol-1-yl)benzaldehydeYield 54%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent

Procedure

A mixture comprising 9.25 g of 3-bromobenzaldehyde, 20.4 g of imidazole, 0.31 g of copper powder and 50 ml of water was heated under reflux in a nitrogen atmosphere for 3 days, followed by the addition of aqueous ammonia. The obtained mixture was extracted with chloroform. The extract was purified by silica gel column chromatography (solvent: methylene chloride/methanol) to obtain 4.61 g of the title compound as a pale yellow crystal (yield: 54%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux in a nitrogen atmosphere for 3 days
  3. extractionThe obtained mixture was extracted with chloroform
  4. customThe extract was purified by silica gel column chromatography (solvent: methylene chloride/methanol)

Sources & evidence

ORD record
ord-7d6dd61a686e4c0f81a93be8361ce33f
Source dataset
uspto-grants-1993_01
Patent number
US05177089

Reaction notes

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