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

HRID 1811443Notes

Reaction equation

HRID 1811443 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5223a30293f047a6ab7f8683e7af3ac2
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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