Thiazolidinedione → HCID 86613944, compound

HRID 504036Notes

Reaction equation

HRID 504036 reaction equation
[CH2:1]([N:8]1[C:17]2[C:16]([OH:18])=[CH:15][CH:14]=[C:13]([CH:19]=O)[C:12]=2[CH2:11][CH2:10][C:9]1=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:22]1[CH2:26][C:25](=[O:27])[NH:24][C:23]1=[O:28]>C1(C)C=CC=CC=1.N1CCCCC1.C(O)(=O)C>[CH2:1]([N:8]1[C:17]2[C:12](=[C:13]([CH:19]=[C:26]3[S:22][C:23](=[O:28])[NH:24][C:25]3=[O:27])[CH:14]=[CH:15][C:16]=2[OH:18])[CH2:11][CH2:10][C:9]1=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 5437ThiazolidinedioneHCID 86613945HCID 86613945, compound

Product 1

HCID 86613944HCID 86613944, compoundYield 99.8%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 8082PiperidineCatalystHCID 1140TolueneSolvent

Procedure

2.0 g of 1-benzyl-8-hydroxy-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde and 0.874 g of 2,4-thiazolidinedione were suspended in 20 ml of toluene. Ten drops of piperidine and ten drops of acetic acid were added, followed by heating and refluxing for 8 hours. The resultant was allowed to cool to precipitate a solid, and the precipitated solid was collected by filtration and dried, giving 2.7 g (92% yield) of 5-(1-benzyl-8-hydroxy-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethylidene)thiazolidine-2,4-dione as a yellow powder.

Workup

  1. temperatureby heating
  2. temperaturerefluxing for 8 hours
  3. temperatureto cool
  4. customto precipitate a solid
  5. filtrationthe precipitated solid was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-f87c42607ffd40a2be0671ced152e0e4
Source dataset
uspto-grants-2010_08
Patent number
US07777038B2

Reaction notes

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