5-{4-[2-(6-Methyl-2-pyridyl)ethoxy]benzylidene}-2,4-thiazolidinedione → 5-{4-[2-(6-Methyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione

HRID 1194075Notes

Reaction equation

HRID 1194075 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][O:10][C:11]2[CH:24]=[CH:23][C:14]([CH:15]=[C:16]3[S:20][C:19](=[O:21])[NH:18][C:17]3=[O:22])=[CH:13][CH:12]=2)[CH:5]=[CH:4][CH:3]=1>O1CCOCC1.[Pd]>[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][O:10][C:11]2[CH:24]=[CH:23][C:14]([CH2:15][CH:16]3[S:20][C:19](=[O:21])[NH:18][C:17]3=[O:22])=[CH:13][CH:12]=2)[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 543908955-{4-[2-(6-Methyl-2-pyridyl)ethoxy]benzylidene}-2,4-thiazolidinedione

Product 1

HCID 129442135-{4-[2-(6-Methyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 5-{4-[2-(6-methyl-2-pyridyl)ethoxy]benzylidene}-2,4-thiazolidinedione (400 mg) in dioxane (60 ml) was added 5% palladium on carbon (1.2 g) and catalytic reduction was carried out at atmospheric pressure for 6 hours. The catalyst was filtered off and the filtrate was concentrated. The residue was recrystallized from 70% ethanol to give 5-{4-[2-(6-methyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione as crystals. Yield: 218 mg (54.2%); m.p.: 156°-157° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was recrystallized from 70% ethanol

Sources & evidence

ORD record
ord-02c70f4713a54188af01560607575f89
Source dataset
uspto-grants-1989_03
Patent number
US04812570

Reaction notes

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