HCID 54166943, compound → 2-(3-Methyl-2,5-dioxohexyl)-1H-isoindole-1,3(2H)-dione

HRID 1863512Notes

Reaction equation

HRID 1863512 reaction equation
[CH3:1][C:2](=[CH:17][C:18](=[O:20])[CH3:19])[C:3](=[O:16])[CH2:4][N:5]1[C:9](=[O:10])[C:8]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:7]2[C:6]1=[O:15]>[Ni].C(OCC)(=O)C>[CH3:1][CH:2]([CH2:17][C:18](=[O:20])[CH3:19])[C:3](=[O:16])[CH2:4][N:5]1[C:9](=[O:10])[C:8]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:7]2[C:6]1=[O:15]

Participants

4

Reactant 1

HCID 54166943HCID 54166943, compound

Product 1

HCID 155638332-(3-Methyl-2,5-dioxohexyl)-1H-isoindole-1,3(2H)-dioneYield 98%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3-Methyl-1-phthalimidohex-3-ene-2,5-dione (423 mg, 1.56 millimoles) was catalytically hydrogenated with 300 mg of Raney nickel (containing ethanol) in 45 ml ethyl acetate using a catalytic reduction apparatus. In 12 minutes, hydrogen was absorbed in an amount stoichiometrically required to hydrogenate the carbon-carbon double bond of the above compound. The catalyst was separated by suction filtration with a care taken not to bring it into contact with the air. The solvent was evaporated from the filtrate under reduced pressure to afford 416 mg of 3-methyl-1-phthalimidohexane-2,5-dione as white crystals in a yield of 98%. Recrystallization from methanol afforded colorless prisms having a melting point of 101.5° to 102.5° C. The spectral data and the results of elemental analysis of the product were as follows:

Workup

  1. customhydrogen was absorbed in an amount
  2. customThe catalyst was separated by suction filtration with a care
  3. customThe solvent was evaporated from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-ca972a8721664425ab7c08f169be7cd5
Source dataset
uspto-grants-1979_09
Patent number
US04169150

Reaction notes

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