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 1811438Notes

Reaction equation

HRID 1811438 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-764af3c9389e404d917092412fdb360f
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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