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

HRID 1811441Notes

Reaction equation

HRID 1811441 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[N:11]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([O:22][CH3:23])=[O:21])=[CH:16][CH:15]=3)[C:10](=[O:24])[CH2:9][CH2:8][C:7]=2[C:6]([CH:25]=O)=[CH:5][CH:4]=1.[S:27]1[CH2:31][C:30](=[O:32])[NH:29][C:28]1=[O:33]>C1(C)C=CC=CC=1.N1CCCCC1.C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:25]=[C:31]2[S:27][C:28](=[O:33])[NH:29][C:30]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

6

Reactant 2

HCID 5437ThiazolidinedioneHCID 866139251-(4-Carbomethoxybenzyl)-8-methoxy-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde

Product 1

HCID 866139415-[8-Methoxy-1-(4-methoxycarbonyl benzyl)-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethylidene]thiazolidine-2,4-dioneYield 90%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 8082PiperidineCatalystHCID 1140TolueneSolvent

Procedure

7.0 g of 8-methoxy-1-(4-methoxycarbonylbenzyl)-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde and 3.25 g of 2,4-thiazolidinedione were suspended in 70 ml of toluene. Ten drops of piperidine and ten drops of acetic acid were added, followed by heating and refluxing for 4 hours. The resultant was allowed to cool to precipitate a solid, and the precipitated solid was collected by filtration and dried, giving 8.0 g (90% yield) of 5-[8-methoxy-1-(4-methoxycarbonylbenzyl)-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethylidene]thiazolidine-2,4-dione as a light yellow powder.

Workup

  1. temperatureby heating
  2. temperaturerefluxing for 4 hours
  3. temperatureto cool
  4. customto precipitate a solid
  5. filtrationthe precipitated solid was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-126f021bd8a941ee8568e13c31910473
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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