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

HRID 324012

Reaction equation

HRID 324012 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-110651ec896446af9e47db84dcfbe273
Source dataset
uspto-grants-2001_04
Patent number
US06214996B1

Linked notes

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