4-(Bromomethyl)-1,2-dihydroquinolin-2-one → Diethyl 2-(4-chlorobenzamido)-2-((2-oxo-1,2-dihydroquinolin-4-yl)methyl)malonate

HRID 1840640

Reaktionsgleichung

Reaktionsgleichung von HRID 1840640
[O-]CC.[Na+].[Cl:5][C:6]1[CH:25]=[CH:24][C:9]([C:10]([NH:12][CH:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:11])=[CH:8][CH:7]=1.Br[CH2:27][C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[NH:31][C:30](=[O:38])[CH:29]=1>C(O)C>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([C:10]([NH:12][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])([CH2:27][C:28]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[NH:31][C:30](=[O:38])[CH:29]=2)[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:11])=[CH:24][CH:25]=1

Komponenten

5

Edukt 3

HCID 2682964-(Bromomethyl)-1,2-dihydroquinolin-2-oneHCID 2723922Sodium ethoxideHCID 13540809Diethyl (4-chlorobenzamido)propanedioate

Produkt 1

HCID 11465574Diethyl 2-(4-chlorobenzamido)-2-((2-oxo-1,2-dihydroquinolin-4-yl)methyl)malonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

100 ml of anhydrous ethyl alcohol and 2.23 g of sodium ethoxide (96%) were added to a 500 ml flask, and the mixture was cooled down to below 5° C. After adding 7.91 g of diethyl 4-chlorobenzamidomalonate, the resulting solution was stirred at below 5° C. for one hour. 5.00 g of 4-bromomethylquinolinon was added to the mixture and the resulting solution was stirred at the room temperature for 16 hours to produce an intermediate, ethyl 2-(4-chlorobenzoylamino)-2-ethoxycarbonyl-3-[2(1H)-quinolinon-4-yl]propionate. After the completion of the reaction, 2.71 g of sodium hydroxide (93%) was dissolved in 30 ml of purified water and this aqueous solution was added to the above solution, which was then stirred at the room temperature for about 2 hours. Subsequently, the resulting solution was warmed to about 60° C. and stirred for 2 hours to complete the reaction. The ethyl alcohol was removed through vacuum concentration, and purified water and 1N HCl were added to the residue for crystallization. The crystal thus obtained was filtered and then subjected to recrystallization with DMF and water to yield 7.18 g (92.17%) of 2-(4-chlorobenzoylamino)-3-[2(1H)-quinolinon-4-yl]propionic acid.

Aufarbeitung

  1. temperaturethe mixture was cooled down to below 5° C
  2. stirringthe resulting solution was stirred at the room temperature for 16 hours

Quellen und Nachweise

ORD-Eintrag
ord-54c3f566bd4348ba9de67964ee571ece
Quelldatensatz
uspto-grants-2004_01
Patentnummer
US06680386B2

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