Ethanol → 6,8-Dichloro-3-hydroxy-2-[1,1'-biphenyl]-4-yl-4-quinolinecarboxylic acid

HRID 231651

Reaktionsgleichung

Reaktionsgleichung von HRID 231651
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([Cl:11])[CH:10]=1)[NH:7][C:6](=O)[C:5]2=[O:13].[OH-:14].[Na+].C(OCC([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=O)(=O)C.[CH2:35]([OH:37])[CH3:36]>O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([Cl:11])[CH:10]=1)[N:7]=[C:6]([C:32]1[CH:33]=[CH:34][C:29]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:23]=3)=[CH:30][CH:31]=1)[C:5]([OH:13])=[C:36]2[C:35]([OH:14])=[O:37]

Komponenten

6

Edukt 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 807715,7-Dichloro-1H-indole-2,3-dioneHCID 20034058Acetic acid 2-biphenyl-2-yl-2-oxo-ethyl ester

Produkt 1

HCID 144981606,8-Dichloro-3-hydroxy-2-[1,1'-biphenyl]-4-yl-4-quinolinecarboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

A suspension of 21 g of 5,7-dichloro-2,3-indolinedione in 120 ml of water was treated with a sufficient amount of a solution of 16.6 g of sodium hydroxide in 55 ml of water to provide solution. A warm solution of 25.4 g of acetoxyacetylbiphenyl in 350 ml of ethanol was added, followed by the balance of the alkali solution. The mixture was refluxed for 2.5 hours. During the last 1/2 hour 50 ml of ethanol was distilled off. A 300 ml portion of water was added, the mixture was stirred, cooled and filtered through diatomaceous earth. The solid was taken up in 1500 ml of water containing 100 ml of 10N sodium hydroxide, filtered and the filtrate treated with 32 ml of concentrated hydrochloric acid and 10 ml of glacial acetic acid. The resulting solid was dissolved in 400 ml of hot cellosolve, filtered and precipitated with water, giving 18.5 g of the desired product, mp 215°-217° C.

Aufarbeitung

  1. customto provide solution
  2. temperatureThe mixture was refluxed for 2.5 hours
  3. distillationDuring the last 1/2 hour 50 ml of ethanol was distilled off
  4. additionA 300 ml portion of water was added
  5. temperaturecooled
  6. filtrationfiltered through diatomaceous earth
  7. filtrationfiltered
  8. additionthe filtrate treated with 32 ml of concentrated hydrochloric acid and 10 ml of glacial acetic acid
  9. dissolutionThe resulting solid was dissolved in 400 ml of hot cellosolve
  10. filtrationfiltered
  11. customprecipitated with water

Quellen und Nachweise

ORD-Eintrag
ord-3290670892e649a589de0ba37439b6b0
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04847381

Verknüpfte Notizen

Wird geladen…