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

HRID 1840641

반응식

HRID 1840641 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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 methanol and potassium hydroxide to yield 6.7 g (86.0%) of 2-(4-chlorobenzoylamino)-3-[2(1H)-quinolinon-4-yl]propionic acid.

후처리

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

출처 및 근거

ORD 기록
ord-da6ed6017efa4967828abf878fbba424
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06680386B2

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