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

HRID 1840643

Reaktionsgleichung

Reaktionsgleichung von HRID 1840643
[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 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 4 hours to complete the reaction. The concentrated hydrochloric acid were added to the residue for crystallization. The crystal thus obtained was filtered and then subjected to recrystallization with DMF and water to yield 7.15 g (91.78%) 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-61b7e6d74df349ada2f0f8ff582ab5c3
Quelldatensatz
uspto-grants-2004_01
Patentnummer
US06680386B2

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