Thiazolidinedione → 5-(1-Carboxymethyl-8-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl)thiazolidine-2,4-dione

HRID 1811449Notes

Reaction equation

HRID 1811449 reaction equation
C([O:5][C:6]([CH2:8][N:9]1[C:18]2[C:17]([O:19][CH3:20])=[CH:16][CH:15]=[C:14]([CH:21]=O)[C:13]=2[CH2:12][CH2:11][C:10]1=[O:23])=[O:7])(C)(C)C.[S:24]1[CH2:28][C:27](=[O:29])[NH:26][C:25]1=[O:30].N1C=CC=CC1>C1(C)C=CC=CC=1.C(O)(=O)C.N1CCCCC1>[C:6]([CH2:8][N:9]1[C:18]2[C:13](=[C:14]([CH2:21][CH:28]3[S:24][C:25](=[O:30])[NH:26][C:27]3=[O:29])[CH:15]=[CH:16][C:17]=2[O:19][CH3:20])[CH2:12][CH2:11][C:10]1=[O:23])([OH:5])=[O:7]

Participants

7

Reactant 3

HCID 5437ThiazolidinedioneHCID 407038DihydropyridinesHCID 866139491-Tert-butoxycarbonylmethyl-8-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-5-carboxaldehyde

Product 1

HCID 866139485-(1-Carboxymethyl-8-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl)thiazolidine-2,4-dioneYield 44.9%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 8082PiperidineCatalystHCID 1140TolueneSolvent2×

Procedure

4.16 g of 1-tert-butoxycarbonylmethyl-8-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-5-carboxaldehyde and 1.66 g of 2,4-thiazolidinedione (1.00 eq.) were suspended in 40 ml of toluene, and two drops of acetic acid and two drops of piperidine were added, followed by heating and refluxing for 13 hours using a Dean Stark trap. After cooling, crystals were separated by filtration and washed with toluene. The crystals obtained were suspended in 3.15 g of silica gel, 2.09 g of dihydropyridine, and 60 ml of toluene, followed by heating and refluxing overnight. 3.15 g of silica gel was added, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1), and recrystallized from ethyl acetate-hexane, giving 2.13 g (38% yield) of 5-(1-carboxymethyl-8-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl)thiazolidine-2,4-dione as a white powder.

Workup

  1. temperatureby heating
  2. temperaturerefluxing for 13 hours
  3. temperatureAfter cooling
  4. customcrystals were separated by filtration
  5. washwashed with toluene
  6. customThe crystals obtained
  7. temperatureby heating
  8. temperaturerefluxing overnight
  9. addition3.15 g of silica gel was added
  10. distillationthe solvent was distilled off under reduced pressure
  11. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1)
  12. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-6a935d6edea74ec6bfb9d2a0e9e34310
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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