Acetic Acid → 1-[2-(2-Oxo-1,2-dihydroquinolin-1-yl)-4-pyridyl]-2,3-bis(methoxycarbonyl)-6,7-dimethoxynaphthalene

HRID 324012

Reaktionsgleichung

Reaktionsgleichung von HRID 324012
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:19][CH3:20])=[C:14]([O:17][CH3:18])[CH:15]=3)[CH:10]=[C:9]([C:21]([O:23][CH3:24])=[O:22])[C:8]=2[C:25]([O:27][CH3:28])=[O:26])=[CH:3][CH:2]=1.Cl[C:30]1[CH:39]=[CH:38][C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:31]=1.Br.C(O)(=[O:43])C>C1(C)C=CC=CC=1>[O:43]=[C:30]1[CH:39]=[CH:38][C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:31]1[C:2]1[CH:3]=[C:4]([C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:19][CH3:20])=[C:14]([O:17][CH3:18])[CH:15]=3)[CH:10]=[C:9]([C:21]([O:23][CH3:24])=[O:22])[C:8]=2[C:25]([O:27][CH3:28])=[O:26])[CH:5]=[CH:6][N:1]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 119282-ChloroquinolineHCID 117286421-(4-Pyridyl)-2,3-bis(methoxycarbonyl)-6,7-dimethoxynaphthalene

Produkt 1

HCID 220074481-[2-(2-Oxo-1,2-dihydroquinolin-1-yl)-4-pyridyl]-2,3-bis(methoxycarbonyl)-6,7-dimethoxynaphthalene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a suspension of 1-(4-pyridyl)-2,3-bis(methoxycarbonyl)-6,7-dimethoxynaphthalen, N-oxide (1.99 g) in toluene (10 ml) is added 2-chloroquinoline (3.27 g). To the mixture is added five drops of a 30 % solution of hydrogen bromide in acetic acid, and the mixture is refluxed for 15 hours. After the mixture is concentrated under reduced pressure to remove the solvent, water and methylene chloride are added to the residue. The pH value e of the mixture is adjusted to pH 8 with an aqueous sodium hydrogen carbonate solution. The mixture is extracted with methylene chloride, and the extract is washed, dried and concentrated under reduced pressure to remove the solvent. The residue is purified by silica gel column chromatography (solvent; chloroform:acetone=4:1) to give 1-[2-(2-oxo-1,2-dihydroquinolin-1-yl)-4-pyridyl]-2,3-bis(methoxycarbonyl)-6,7-dimethoxynaphthalene (2.60 g).

Aufarbeitung

  1. temperaturethe mixture is refluxed for 15 hours
  2. concentrationAfter the mixture is concentrated under reduced pressure
  3. customto remove the solvent, water and methylene chloride
  4. additionare added to the residue
  5. extractionThe mixture is extracted with methylene chloride
  6. washthe extract is washed
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customto remove the solvent
  10. customThe residue is purified by silica gel column chromatography (solvent; chloroform:acetone=4:1)

Quellen und Nachweise

ORD-Eintrag
ord-110651ec896446af9e47db84dcfbe273
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06214996B1

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