5-[8-Methoxy-1-(4-methoxycarbonyl benzyl)-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethylidene]thiazolidine-2,4-dione → 5-[8-Methoxy-1-(4-methoxycarbonylbenzyl)-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl]thiazolidine-2,4-dione

HRID 504033Notes

Reaction equation

HRID 504033 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:25]=[C:26]2[S:30][C:29](=[O:31])[NH:28][C:27]2=[O:32])=[C:7]2[C:12]=1[N:11]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([O:22][CH3:23])=[O:21])=[CH:16][CH:15]=1)[C:10](=[O:24])[CH2:9][CH2:8]2>[C].[Pd].CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:25][CH:26]2[S:30][C:29](=[O:31])[NH:28][C:27]2=[O:32])=[C:7]2[C:12]=1[N:11]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([O:22][CH3:23])=[O:21])=[CH:16][CH:15]=1)[C:10](=[O:24])[CH2:9][CH2:8]2

Participants

4

Reactant 1

HCID 866139415-[8-Methoxy-1-(4-methoxycarbonyl benzyl)-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethylidene]thiazolidine-2,4-dione

Product 1

HCID 580267165-[8-Methoxy-1-(4-methoxycarbonylbenzyl)-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl]thiazolidine-2,4-dioneYield 74.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

7.0 g of 10% palladium carbon was added to a DMF solution (70 ml) of 7.0 g of 5-[8-methoxy-1-(4-methoxycarbonyl benzyl)-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethylidene]thiazolidine-2,4-dione, and a catalytic reduction was carried out at 40° C. for 5 hours. The catalyst was removed by filtration and the filtrate was concentrated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1→1:1). The purified product was recrystallized from an ethyl acetate-diethyl ether mixed solvent, giving 5.23 g (74% yield) of 5-[8-methoxy-1-(4-methoxycarbonylbenzyl)-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl]thiazolidine-2,4-dione as a white powder.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1→1:1)
  4. customThe purified product was recrystallized from an ethyl acetate-diethyl ether mixed solvent

Sources & evidence

ORD record
ord-d76c40c909804d9890c08ce35d0db354
Source dataset
uspto-grants-2010_08
Patent number
US07777038B2

Reaction notes

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