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

HRID 726296

반응식

HRID 726296 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 66611,3-Dimethyl-2-imidazolidinone용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-69ad495e42c24af4becee84e24612468
출처 데이터셋
uspto-grants-1998_01
특허 번호
US05708173

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