Potassium Iodide → HCID 86732736、化合物

HRID 525869ノート

反応式

HRID 525869 の反応式
[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]

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 136341437HCID 136341437、化合物

生成物 1

HCID 86732736HCID 86732736、化合物収率 137.9%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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.

後処理

  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%)

出典と根拠

ORDレコード
ord-5aff58366bf9426c994d4e2ebbe16841
出典データセット
uspto-grants-2016_05
特許番号
US09340556B2

反応ノート

読み込み中…