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

HRID 726296

Reaction equation

HRID 726296 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-69ad495e42c24af4becee84e24612468
Source dataset
uspto-grants-1998_01
Patent number
US05708173

Linked notes

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