Potassium Iodide → HCID 86732736, 화합물

HRID 525869노트

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HRID 525869 반응식
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([OH:14])=[C:10]([OH:13])[CH:11]=2)[C:6](=[O:15])[C:5]([C:16]([O:18][CH3:19])=[O:17])=[N:4]1)[CH3:2].[C:20](=[O:23])([O-])[O-].[K+].[K+].[I-].[K+].Cl[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=1>CC(C)=O>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([O:14][CH2:6][C:7]3[CH:12]=[CH:11][C:10]([O:23][CH3:20])=[CH:9][CH:8]=3)=[C:10]([O:13][CH2:29][C:30]3[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=3)[CH:11]=2)[C:6](=[O:15])[C:5]([C:16]([O:18][CH3:19])=[O:17])=[N:4]1)[CH3:2]

참가 물질

6

반응물 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 136341437HCID 136341437, 화합물

생성물 1

HCID 86732736HCID 86732736, 화합물수율 137.9%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a suspension of methyl 1-ethyl-6,7-dihydroxy-4-oxo-1,4-dihydrocinnoline-3-carboxylate (11 g, 35.8 mmol), potassium carbonate (16.33 g, 118 mmol) and potassium iodide (1.189 g, 7.16 mmol) in acetone (200 mL) at room temperature, was added 1-(chloromethyl)-4-methoxybenzene (16.82 g, 107 mmol). The mixture was then heated to reflux overnight. After cooling to room temperature, the mixture was concentrated in vacuo and the residue was partitioned between dichloromethane and brine. The organic phase was separated, and the aqueous phase was extracted with dichloromethane several times. The combined organic extracts were dried over sodium sulfate, filtered and concentrated. The residue was purified by automatic silica gel column chromatography (Combiflash RF) eluting with methanol/dichloromethane (0-20%) to afford methyl 1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydrocinnoline-3-carboxylate (15 g, 24.68 mmol, 68.9% yield) as a light yellow solid. LCMS: (M+H)+: 505.1.

후처리

  1. temperatureThe mixture was then heated
  2. temperatureto reflux overnight
  3. concentrationthe mixture was concentrated in vacuo
  4. customthe residue was partitioned between dichloromethane and brine
  5. customThe organic phase was separated
  6. extractionthe aqueous phase was extracted with dichloromethane several times
  7. dry with materialThe combined organic extracts were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by automatic silica gel column chromatography (Combiflash RF)
  11. washeluting with methanol/dichloromethane (0-20%)

출처 및 근거

ORD 기록
ord-5aff58366bf9426c994d4e2ebbe16841
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340556B2

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