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

HRID 1199137Notes

Reaction equation

HRID 1199137 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]>CN(C)C=O.[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 6228DimethylformamideSolvent

Procedure

To a solution of 5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzylidene}-2,4-thiazolidinedione (600 g) in dimethylformamide (1.2 l) was added palladium on carbon (600 g). The mixture was heated at 50° C. to 55° C. under 50 kg/cm2 for 2 hours. The catalyst was filtered off and water was added to the filtrate. The resulting crystals were collected by filtration and washed with water. Recrystallization from dioxane (8.5 l) gave crystals of 5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione. Yield: 380.9 g (63.1%).

Workup

  1. temperatureThe mixture was heated at 50° C. to 55° C. under 50 kg/cm2 for 2 hours
  2. filtrationThe catalyst was filtered off
  3. additionwater was added to the filtrate
  4. filtrationThe resulting crystals were collected by filtration
  5. washwashed with water
  6. customRecrystallization from dioxane (8.5 l)

Sources & evidence

ORD record
ord-637cd63f00ae41f9864d08fd206d2492
Source dataset
uspto-grants-1990_02
Patent number
US04898947

Reaction notes

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