Acetonitrile → 4,4-Dimethyl-1,3(2H,4H)-isoquinolinedione

HRID 2228966Notes

Reaction equation

HRID 2228966 reaction equation
COC1C=CC(C[N:8]2[C:17](=[O:18])[C:16]([CH3:20])([CH3:19])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:21])=CC=1.C(#N)C.[N+]([O-])([O-])=O.[Ce+3].[NH4+].[NH4+].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O>O>[CH3:19][C:16]1([CH3:20])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:21])[NH:8][C:17]1=[O:18]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 14029277Diammonium cerium nitrateHCID 185109392-[(4-Methoxyphenyl)methyl]-4,4-dimethyl-1,3(2H,4H)-isoquinolinedione

Product 1

HCID 3380304,4-Dimethyl-1,3(2H,4H)-isoquinolinedioneYield 297%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The compound (6.0 g) obtained in step (b) just above was dissolved in a mixed solvent (acetonitrile:water=4:1) (40 ml). Diammonium cerium nitrate (26.6 g) was added to the solution. The mixture was stirred at room temperature for 3 hr. The reaction solution was extracted with ethyl acetate. The organic layer was then dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=8:2) to give 4,4-dimethyl-4H-isoquinoline-1,3-dione (10.9 g).

Workup

  1. extractionThe reaction solution was extracted with ethyl acetate
  2. dry with materialThe organic layer was then dried over anhydrous magnesium sulfate
  3. customThe solvent was then removed by distillation under the reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=8:2)

Sources & evidence

ORD record
ord-f9924bbc406b4eff8aa6a1756a5dd3c8
Source dataset
uspto-grants-2002_07
Patent number
US06417362B1

Reaction notes

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