5-(4-(2-(5-Ethylpyridin-2-yl)ethoxy)benzylidene)thiazolidine-2,4-dione → Pioglitazone

HRID 1199138Notes

Reaction equation

HRID 1199138 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:25]=[CH:24][C:15]([CH:16]=[C:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:23])=[CH:14][CH:13]=2)=[N:7][CH:8]=1)[CH3:2]>O1CCOCC1.[Pd]>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:25]=[CH:24][C:15]([CH2:16][CH:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:23])=[CH:14][CH:13]=2)=[N:7][CH:8]=1)[CH3:2]

Participants

4

Reactant 1

HCID 533948925-(4-(2-(5-Ethylpyridin-2-yl)ethoxy)benzylidene)thiazolidine-2,4-dione

Product 1

HCID 4829Pioglitazone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzylidene}-2,4-thiazolidinedione (10 g) in dioxane (200 ml) was added 5% palladium on carbon (5 g). The mixture was heated at 100° C. under 50 kg/cm2 for 2 hours. The catalyst was filtered off, and the filtrate was concentrated to about 70 ml under reduced pressure. The resulting crystals were collected by filtration and dried at 50° C. under a reduced pressure to give 7.2 g of crude crystals. Recrystallization from acetic acid-water gave crystals of 5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione. Yield: 6.42 g (63.8%).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated to about 70 ml under reduced pressure
  3. filtrationThe resulting crystals were collected by filtration
  4. customdried at 50° C. under a reduced pressure
  5. customto give 7.2 g of crude crystals
  6. customRecrystallization from acetic acid-water

Sources & evidence

ORD record
ord-c4c028f6dade4af8a313d045d9fe1768
Source dataset
uspto-grants-1990_02
Patent number
US04898947

Reaction notes

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