HCID 53900518, compound → HCID 9801620, compound

HRID 849012Notes

Reaction equation

HRID 849012 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[N:4]([CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([CH:22]=[C:23]3[S:27][C:26](=[O:28])[NH:25][C:24]3=[O:29])=[CH:18][CH:17]=2)[N:3]=1.[H][H]>O1CCOCC1.[Pd]>[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[N:4]([CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH:23]3[S:27][C:26](=[O:28])[NH:25][C:24]3=[O:29])=[CH:18][CH:17]=2)[N:3]=1

Participants

5

Reactant 2

HCID 53900518HCID 53900518, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9801620HCID 9801620, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

##STR41## A solution of 5-[4-[2-[4-methyl-1-oxo-1,2-dihydro-phthalazin-2-yl]ethoxy]phenyl methylene] thiazolidin-2,4-dione (9.0 g, 22.0 mmoles) obtained in example 1, in 1,4-dioxane (500 mL) was reduced with hydrogen in the presence of 10% palladium on charcoal (22.5 g) at 60 psi for 48 h. The mixture was filtered through a bed of celite. The filtrate was evaporated to dryness under reduced pressure. The crude compound was recrystallised using CH2Cl2 /pet. ether to afford the title compound (7.2 g, 80%). mp: 170° C.

Workup

  1. filtrationThe mixture was filtered through a bed of celite
  2. customThe filtrate was evaporated to dryness under reduced pressure
  3. customThe crude compound was recrystallised

Sources & evidence

ORD record
ord-438be4e9d1e148c3bb179800773befd1
Source dataset
uspto-grants-2000_01
Patent number
US06011036

Reaction notes

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