HCID 86613944, compound → HCID 86613946, compound

HRID 1811446Notes

Reaction equation

HRID 1811446 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[C:13]([CH:19]=[C:20]3[S:24][C:23](=[O:25])[NH:22][C:21]3=[O:26])[CH:14]=[CH:15][C:16]=2[OH:18])[CH2:11][CH2:10][C:9]1=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[C].[Pd].CN(C=O)C>[CH2:1]([N:8]1[C:17]2[C:12](=[C:13]([CH2:19][CH:20]3[S:24][C:23](=[O:25])[NH:22][C:21]3=[O:26])[CH:14]=[CH:15][C:16]=2[OH:18])[CH2:11][CH2:10][C:9]1=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 86613944HCID 86613944, compound

Product 1

HCID 86613946HCID 86613946, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

2.2 g of 10% palladium carbon was added to a DMF solution (20 ml) of 2.2 g of 5-(1-benzyl-8-hydroxy-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethylidene)thiazolidine-2,4-dione, and the mixture was subjected to catalytic reduction at room temperature for 2 hours. The catalyst was removed by filtration, and the filtrate was concentrated. The residue was dissolved in ethyl acetate, washed with water and saturated sodium chloride solution, and concentrated. The residue was purified by silica gel column chromatography (dichloromethane:methanol=50:1). The purified product was recrystallized from a dichloromethane-ether mixed solvent, giving 1.9 g (88% yield) of 5-(1-benzyl-8-hydroxy-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl)thiazolidine-2,4-dione as a white powder.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water and saturated sodium chloride solution
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (dichloromethane:methanol=50:1)
  7. customThe purified product was recrystallized from a dichloromethane-ether mixed solvent

Sources & evidence

ORD record
ord-0d2a3e886f3c4b0b94ab56945bdcc1c5
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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