3-(4,5-dihydro-1H-imidazol-2-yl)pyridine → 3-(1H-Imidazol-2-yl)pyridine

HRID 1388386Notes

Reaction equation

HRID 1388386 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[NH:8][CH2:9][CH2:10][N:11]=2)[CH:2]=1.[Mn]([O-])([O-])(=O)=O.[Ba+2]>C(Cl)Cl>[NH:8]1[CH:9]=[CH:10][N:11]=[C:7]1[C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 2380793-(4,5-dihydro-1H-imidazol-2-yl)pyridineHCID 3084030Barium manganate

Product 1

HCID 123955003-(1H-Imidazol-2-yl)pyridineYield 65.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(3-pyridyl)imidazoline (7.2 g, 0.049 M), and barium manganate (52.5 g) in CH2Cl2 (500 ml) were refluxed for 24 hrs. The reaction mixture was then filtered through diatomaceous earth, washed with ethylacetate (3×200 ml) and methanol (3×100 ml). The combined filtrates were concentrated to yield an oil which was purified on silica gel column, eluted with 20% by volume methanol 80% by volume methylene dichloride, to give 3-(1H-imidazol-2-yl)pyridine (4.66 g, 64.7%).

Workup

  1. filtrationThe reaction mixture was then filtered through diatomaceous earth
  2. washwashed with ethylacetate (3×200 ml) and methanol (3×100 ml)
  3. concentrationThe combined filtrates were concentrated
  4. customto yield an oil which
  5. customwas purified on silica gel column
  6. washeluted with 20% by volume methanol 80% by volume methylene dichloride

Sources & evidence

ORD record
ord-f27d69c5337a4b47b0d2a3c9c63d9ba7
Source dataset
uspto-grants-1984_02
Patent number
US04431653

Reaction notes

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