Hantzsch ester → HCID 86613936, compound

HRID 504027Notes

Reaction equation

HRID 504027 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([CH:17]=[C:18]3[S:22][C:21](=[O:23])[NH:20][C:19]3=[O:24])=[CH:9][C:8]2=[O:25])=[CH:4][CH:3]=1.CC1NC(C)=C(C(OCC)=O)CC=1C(OCC)=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([CH2:17][CH:18]3[S:22][C:21](=[O:23])[NH:20][C:19]3=[O:24])=[CH:9][C:8]2=[O:25])=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 70849Hantzsch esterHCID 86613934HCID 86613934, compound

Product 1

HCID 86613936HCID 86613936, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.96 g of 5-[1-(4-chlorobenzyl)-2-oxo-1,2-dihydroquinolin-4-ylmethylidene]thiazolidine-2,4-dione, 0.735 g of diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate, and 0.96 g of silica gel were added to 30 ml of toluene, followed by heating and refluxing overnight. The solvent was distilled off, and the residue was purified by silica gel column chromatography (dichloromethane:ethyl acetate of 10:1→3:1), and the purified product was recrystallized from a chloroform-ether mixed solvent, giving 0.87 g (91% yield) of 5-[1-(4-chlorobenzyl)-2-oxo-1,2-dihydroquinolin-4-ylmethyl]thiazolidine-2,4-dione as a white powder.

Workup

  1. temperatureby heating
  2. temperaturerefluxing overnight
  3. distillationThe solvent was distilled off
  4. customthe residue was purified by silica gel column chromatography (dichloromethane:ethyl acetate of 10:1→3:1)
  5. customthe purified product was recrystallized from a chloroform-ether mixed solvent

Sources & evidence

ORD record
ord-51c9b07316424c429a989bfd8d78c0d7
Source dataset
uspto-grants-2010_08
Patent number
US07777038B2

Reaction notes

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