Dichloromethane → HCID 86732794, 화합물

HRID 525926노트

반응식

HRID 525926 반응식
[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]

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 136341439HCID 136341439, 화합물

생성물 1

HCID 86732794HCID 86732794, 화합물수율 84.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-0c1ddc456fa14d539bae1a3b8c193b7a
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340556B2

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