Dichloromethane → HCID 86732794、化合物

HRID 525926ノート

反応式

HRID 525926 の反応式
[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]

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 136341439HCID 136341439、化合物

生成物 1

HCID 86732794HCID 86732794、化合物収率 84.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-0c1ddc456fa14d539bae1a3b8c193b7a
出典データセット
uspto-grants-2016_05
特許番号
US09340556B2

反応ノート

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