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

HRID 1959541Notes

Reaction equation

HRID 1959541 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>O1CCOCC1>[N:14]1([C:2]2[C:11]3[C:6](=[C:7]([OH:12])[CH:8]=[CH:9][CH:10]=3)[N:5]=[C:4]([CH3:13])[CH:3]=2)[CH:18]=[CH:17][N:16]=[CH:15]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 122197224-Chloro-8-hydroxy-2-methylquinoline

Product 1

HCID 184042364-(1H-Imidazol-1-yl)-2-methylquinolin-8-ol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-chloro-2-methyl-quinolin-8-ol (2.0 g, 10 mmol) and imidazole (3.53 g, 51.8 mmol) in dioxane (20 mL) was heated to reflux for 28 h. The solvent was removed in vacuo and the residue was purified by flash chromatography on silica gel (elution with DCM/methanol 10:1) to give the title compound. MS (m/z): 226.3 [M+H+].

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 28 h
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by flash chromatography on silica gel (elution with DCM/methanol 10:1)

Sources & evidence

ORD record
ord-653e6d7c75f54932bd69a4ffcd6a882c
Source dataset
uspto-grants-2013_04
Patent number
US08410134B2

Reaction notes

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