1,4-Dioxane → HCID 67592240, compound

HRID 1779998Notes

Reaction equation

HRID 1779998 reaction equation
[NH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH2:4][CH2:3][C:2]1=[O:11].O1CCOCC1>[Pd].C(O)C>[NH:1]1[C@@H:10]2[C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][C:2]1=[O:11]

Participants

5

Reactant 2

HCID 312751,4-DioxaneHCID 7360043,4,5,6,7,8-Hexahydro-2(1H)-quinolinone

Product 1

HCID 67592240HCID 67592240, compoundYield 50.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 1 g of 3,4,5,6,7,8-hexahydro-2(1H)-quinolinone in 1:1 mixture of dioxane and ethanol was hydrogenated in presence of 250 mg of 10% palladium on carbon at 60 psi and room temperature for 4 hours. The catalyst was filtered on a bed of filter cell and washed with dioxane-ethanol mixture. The filtrate was concentrated to give a residue which was purified on silica gel using ethyl acetate as solvent to give 510 mg of the desired product containing about 10% trans-isomer. Recrystallization from hexane did not improve the isomer ratio.

Workup

  1. filtrationThe catalyst was filtered on a bed of filter cell
  2. washwashed with dioxane-ethanol mixture
  3. concentrationThe filtrate was concentrated
  4. customto give a residue which
  5. customwas purified on silica gel

Sources & evidence

ORD record
ord-91ec9b18f6f34d06a648a144d3e99b8f
Source dataset
uspto-grants-1997_05
Patent number
US05629322

Reaction notes

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