Imidazole → 4-(1H-Imidazol-1-yl)-2-methylquinolin-8-ol

HRID 1699183Notes

Reaction equation

HRID 1699183 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([OH:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1.[NH:14]1[CH:18]=[CH:17][N:16]=[CH:15]1.C(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>O1CCOCC1>[OH:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[C:4]([CH3:13])[CH:3]=[C:2]2[N:14]1[CH:18]=[CH:17][N:16]=[CH:15]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6212ChloroformHCID 516892Sodium BicarbonateHCID 122197224-Chloro-8-hydroxy-2-methylquinoline

Product 1

HCID 184042364-(1H-Imidazol-1-yl)-2-methylquinolin-8-olYield 85.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The solution of 4-chloro-8-hydroxy-2-methylquinoline (2.0 g), imidazole (3.52 g) in dioxane (20 ml) was refluxed for 18 hours. The cooled reaction mixture was added chloroform and aqueous sodium bicarbonate solution. The organic layer was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was crystallized from ether to give 8-hydroxy-4-(imidazol-1-yl)-2-methylquinoline (1.99 g) as colorless crystals.

Workup

  1. customThe cooled reaction mixture
  2. washThe organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was crystallized from ether

Sources & evidence

ORD record
ord-0404d57368b54b6a8f0ec0f0bc1fd31a
Source dataset
uspto-grants-2002_02
Patent number
US06344462B1

Reaction notes

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