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Ethanol → 5-[8-Methoxy-1-(4-carboxybenzyl)-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl]thiazolidine-2,4-dione

HRID 1811443
ノート
印刷プレビュー

反応式

HRID 1811443 の反応式
[OH-].[Li+].C(O)C.[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:30][CH:31]2[S:35][C:34](=[O:36])[NH:33][C:32]2=[O:37])=[C:12]2[C:17]=1[N:16]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([O:27]C)=[O:26])=[CH:21][CH:20]=1)[C:15](=[O:29])[CH2:14][CH2:13]2>C1COCC1>[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:30][CH:31]2[S:35][C:34](=[O:36])[NH:33][C:32]2=[O:37])=[C:12]2[C:17]=1[N:16]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]([OH:27])=[O:26])=[CH:23][CH:24]=1)[C:15](=[O:29])[CH2:14][CH2:13]2
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 702EthanolHCID 3939Lithium HydroxideHCID 580267165-[8-Methoxy-1-(4-methoxycarbonylbenzyl)-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl]thiazolidine-2,4-dione

生成物 1

HCID 866139425-[8-Methoxy-1-(4-carboxybenzyl)-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl]thiazolidine-2,4-dione収率 97%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

実験手順

35 ml of an aqueous 1 N-lithium hydroxide solution was added to a mixed ethanol (200 ml) and THF (200 ml) solution of 4.0 g of 5-[8-methoxy-1-(4-methoxycarbonylbenzyl)-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl]thiazolidine-2,4-dione, followed by stirring at room temperature overnight. The solvent was distilled off under reduced pressure, hydrochloric acid was added to the residue, and the insoluble matter thus formed was collected by filtration. The collected insoluble matter was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1→1:3), and recrystallized from ethyl acetate, giving 3.75 g (97% yield) of 5-[8-methoxy-1-(4-carboxybenzyl)-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl]thiazolidine-2,4-dione as a white powder.

後処理

  1. distillationThe solvent was distilled off under reduced pressure, hydrochloric acid
  2. additionwas added to the residue
  3. customthe insoluble matter thus formed
  4. filtrationwas collected by filtration
  5. customThe collected insoluble matter was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1→1:3)
  6. customrecrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-5223a30293f047a6ab7f8683e7af3ac2
出典データセット
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08362252B2

反応ノート

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