二氯甲烷 → HCID 86732794，化合物

HRID 525926笔记

反应方程式

HRID 525926 反应方程式
[Cl:1][C:2]1[C:11]([OH:12])=[C:10]([OH:13])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:19])[C:5]([C:16]([OH:18])=[O:17])=[N:6][N:7]2[CH2:14][CH3:15].[C:20](=[O:23])([O-])[O-].[K+].[K+].Cl[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=1.ClCCl>CN(C)C=O>[Cl:1][C:2]1[C:11]([O:12][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)=[C:10]([O:13][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)[CH:9]=[C:8]2[C:3]=1[C:4](=[O:19])[C:5]([C:16]([O:18][CH2:4][C:3]1[CH:8]=[CH:9][C:10]([O:23][CH3:20])=[CH:11][CH:2]=1)=[O:17])=[N:6][N:7]2[CH2:14][CH3:15]

参与物

6

反应物 4

HCID 6344二氯甲烷HCID 11430碳酸钾HCID 699934-甲氧基氯苄HCID 136341439HCID 136341439，化合物

产物 1

HCID 86732794HCID 86732794，化合物收率 84.6%

试剂、催化剂与溶剂 1

HCID 6228N,N-二甲基甲酰胺溶剂

反应条件

温度
50 °C

实验过程

To a solution of 5-chloro-1-ethyl-6,7-dihydroxy-4-oxo-1,4-dihydrocinnoline-3-carboxylic acid (1.46 g, 5.13 mmol) in N,N-dimethylformamide (DMF) (20 mL) was added potassium carbonate (1.772 g, 12.82 mmol) followed by 1-(chloromethyl)-4-methoxybenzene (1.392 mL, 10.26 mmol). The mixture was heated at 50° C. for 12 h, extracted with ethyl acetate and washed with water, brine, dried over magnesium sulfate. The solvent was removed under vacuum and the residue was chromatographed on ISCO silica column eluting with 0-10% methanol:dichloromethane to afford 4-methoxybenzyl 5-chloro-1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydrocinnoline-3-carboxylate (1.4 g, 2.170 mmol, 42.3% yield). LCMS: (M+H)+: 645.2

后处理

  1. extractionextracted with ethyl acetate
  2. washwashed with water, brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed under vacuum
  5. customthe residue was chromatographed on ISCO silica column
  6. washeluting with 0-10% methanol

来源与证据

ORD记录
ord-0c1ddc456fa14d539bae1a3b8c193b7a
来源数据集
uspto-grants-2016_05
专利号
US09340556B2

反应笔记

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