Diammonium cerium nitrate → 4,4-Dimethyl-1,3(2H,4H)-isoquinolinedione

HRID 1370569Notes

Reaction equation

HRID 1370569 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.[N+]([O-])([O-])=O.[Ce+3].[NH4+].[NH4+].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O>C(#N)C.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

4

Reactant 2

HCID 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 18373917Acetonitrile--water (1/1)Solvent

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-3944a70fab324a0f8f6c5c581df1f809
Source dataset
uspto-grants-2003_06
Patent number
US06583144B2

Reaction notes

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