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Imidazole → 8-Hydroxy-4-(1H-imidazol-yl)-2-methylquinoline

HRID 1871116
Notes
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Reaction equation

HRID 1871116 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

HCID 184042368-Hydroxy-4-(1H-imidazol-yl)-2-methylquinolineYield 85.5%

Reagents, catalysts & solvents 1

HCID 31275
1,4-Dioxane
Solvent

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-e8fde97d78804d8f91a2a3e1c9a84850
Source dataset
uspto-grants-2000_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06100284

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes