HCID 10725990, compound → 4-(1H-Imidazol-1-yl)pyridine

HRID 1193566Notes

Reaction equation

HRID 1193566 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH:11]=[CH:10][NH:9][C:8]2=S)=[CH:3][CH:2]=1>[Ni].[OH-].[NH4+]>[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH:11]=[CH:10][N:9]=[CH:8]2)=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 10725990HCID 10725990, compound

Product 1

HCID 47368114-(1H-Imidazol-1-yl)pyridine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 14923Ammonium HydroxideSolvent

Procedure

An ethanolic solution of 5.9 g (0.028 mol) 1,3-dihydro-1-(4-pyridyl)-2H-imidazole-2-thione prepared in Example 8 is charged with 23.0 g Raney nickel and 10 ml concentrated ammonium hydroxide. The black slurry is refluxed for 2 hours, then filtered to remove the nickel catalyst. The ethanol is removed under vacuum and the product is extracted into CH2Cl2 (2×100 ml). Drying (NaSO4) and concentration gives the 1-(4-pyridyl)-1H-imidazole.

Workup

  1. temperatureThe black slurry is refluxed for 2 hours
  2. filtrationfiltered
  3. customto remove the nickel catalyst
  4. customThe ethanol is removed under vacuum
  5. extractionthe product is extracted into CH2Cl2 (2×100 ml)
  6. customDrying
  7. concentration(NaSO4) and concentration

Sources & evidence

ORD record
ord-99c3d4922ace4710aa3566d262c0e6ae
Source dataset
uspto-grants-1989_03
Patent number
US04810800

Reaction notes

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