Imidazole → 8-Hydroxy-4-(1H-imidazol-yl)-2-methylquinoline
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]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- temperaturewas heated
- temperatureto reflux for 28 h
- customThe solvent was removed in vacuo
- 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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