Veratryl alcohol → 8-Hydroxy-4-(3,4-dimethoxybenzyloxy)-2-methylquinoline

HRID 864575

Reaction equation

HRID 864575 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH2:6][OH:7].[H-].[Na+].Cl[C:16]1[C:25]2[C:20](=[C:21]([OH:26])[CH:22]=[CH:23][CH:24]=2)[N:19]=[C:18]([CH3:27])[CH:17]=1>CN1CCN(C)C1=O>[OH:26][C:21]1[CH:22]=[CH:23][CH:24]=[C:25]2[C:20]=1[N:19]=[C:18]([CH3:27])[CH:17]=[C:16]2[O:7][CH2:6][C:5]1[CH:8]=[CH:9][C:10]([O:11][CH3:12])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

5

Reactant 3

HCID 7118Veratryl alcoholHCID 24758Sodium hydrideHCID 122197224-Chloro-8-hydroxy-2-methylquinoline

Product 1

HCID 221132868-Hydroxy-4-(3,4-dimethoxybenzyloxy)-2-methylquinolineYield 62.8%

Reagents, catalysts & solvents 1

HCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Procedure

To a stirred solution of 3,4-dimethoxybenzyl alcohol (1.68 g) in 1,3-dimethyl-2-imidazolidinone (10 ml) was added sodium hydride (60% in oil, 400 mg) portionwise in an ice-water bath under a nitrogen atmosphere. The mixture was stirred for 30 minutes and then 4-chloro-8-hydroxy-2-methylquinoline (770 mg) was added thereto. The reaction mixture was stirred at 150° C. for 3 hours and cooled to ambient temperature followed by partition into ethyl acetate and water. The organic layer was washed with water twice, dried over magnesium sulfate and evaporated in vacuo. The residue was washed with diethyl ether to give a pale yellow powder (812 mg) of 8-hydroxy-4-(3,4-dimethoxybenzyloxy)-2-methylquinoline.

Workup

  1. stirringThe reaction mixture was stirred at 150° C. for 3 hours
  2. customby partition into ethyl acetate and water
  3. washThe organic layer was washed with water twice
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. washThe residue was washed with diethyl ether

Sources & evidence

ORD record
ord-e4401e4a8059428f98d3750ea6a202cd
Source dataset
uspto-grants-1996_10
Patent number
US05563162

Linked notes

Loading…