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

HRID 504028Notes

Reaction equation

HRID 504028 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:24]=[C: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-:22])=[O:21])=[CH:16][CH:15]=1)[C:10](=[O:23])[CH2:9][CH2:8]2.CC1NC(C)=C(C(OCC)=O)CC=1C(OCC)=O>C1(C)C=CC=CC=1>[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-:22])=[O:21])=[CH:16][CH:15]=1)[C:10](=[O:23])[CH2:9][CH2:8]2

Participants

4

Reactant 2

HCID 70849Hantzsch esterHCID 86613938HCID 86613938, compound

Product 1

HCID 866139375-[8-Methoxy-1-(4-nitrobenzyl)-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl]thiazolidine-2,4-dioneYield 97.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

600 mg of 5-[8-methoxy-1-(4-nitrobenzyl)-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethylidene]thiazolidine-2,4-dione, 415 mg of diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate, and 600 mg of silica gel were added to 20 ml of toluene, followed by heating and refluxing for 14 hours. The solvent was distilled off, and 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-ether mixed solvent, giving 585 mg (97% yield) of 5-[8-methoxy-1-(4-nitrobenzyl)-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl]thiazolidine-2,4-dione as a white powder.

Workup

  1. temperatureby heating
  2. temperaturerefluxing for 14 hours
  3. distillationThe solvent was distilled off
  4. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1→1:1)
  5. customThe purified product was recrystallized from an ethyl acetate-ether mixed solvent

Sources & evidence

ORD record
ord-5f2452bd5d984e4c8f5c6b0ca5084546
Source dataset
uspto-grants-2010_08
Patent number
US07777038B2

Reaction notes

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