5-[8-Methoxy-1-(4-nitrobenzyl)-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl]thiazolidine-2,4-dione → 5-[1-(4-Aminobenzyl)-8-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl]thiazolidine-2,4-dione

HRID 504029Notes

Reaction equation

HRID 504029 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:24][CH:25]2[S:29][C:28](=[O:30])[NH:27][C:26]2=[O:31])=[C:7]2[C:12]=1[N:11]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=1)[C:10](=[O:23])[CH2:9][CH2:8]2>[C].[Pd].CN(C=O)C>[NH2:20][C:17]1[CH:16]=[CH:15][C:14]([CH2:13][N:11]2[C:12]3[C:7](=[C:6]([CH2:24][CH:25]4[S:29][C:28](=[O:30])[NH:27][C:26]4=[O:31])[CH:5]=[CH:4][C:3]=3[O:2][CH3:1])[CH2:8][CH2:9][C:10]2=[O:23])=[CH:19][CH:18]=1

Participants

4

Reactant 1

HCID 866139375-[8-Methoxy-1-(4-nitrobenzyl)-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl]thiazolidine-2,4-dione

Product 1

HCID 866139395-[1-(4-Aminobenzyl)-8-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl]thiazolidine-2,4-dioneYield 86%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

10 g of 10% palladium carbon was added to a DMF solution (100 ml) of 10.0 g of 5-[8-methoxy-1-(4-nitrobenzyl)-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl]thiazolidine-2,4-dione, and the mixture was subjected to a catalytic reduction at 40° C. for 5 hours. The catalyst was removed by filtration, and the filtrate was concentrated. Ethyl acetate and water were added to the residue, and celite filtration was carried out. The filtrate was washed with water and dried over magnesium sulfate, followed by concentration. The residue was purified by silica gel chromatography (n-hexane:ethyl acetate=4:1→1:4), and the purified product was recrystallized from ethyl acetate, giving 7.98 g (86% yield) of 5-[1-(4-aminobenzyl)-8-methoxy-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. additionEthyl acetate and water were added to the residue, and celite filtration
  4. washThe filtrate was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationfollowed by concentration
  7. customThe residue was purified by silica gel chromatography (n-hexane:ethyl acetate=4:1→1:4)
  8. customthe purified product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-91dda30a73bd4d929f39b3b9ff0a9b38
Source dataset
uspto-grants-2010_08
Patent number
US07777038B2

Reaction notes

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