4,4-Dimethyl-1,3(2H,4H)-isoquinolinedione → HCID 21820315, compound

HRID 2228967Notes

Reaction equation

HRID 2228967 reaction equation
[CH3:1][C:2]1([CH3:14])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[NH:4][C:3]1=[O:13].B.[Na].Cl.[CH3:18]O>CO>[CH3:18][O:13][CH:3]1[C:2]([CH3:14])([CH3:1])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[NH:4]1

Participants

5

Reactant 3

HCID 3380304,4-Dimethyl-1,3(2H,4H)-isoquinolinedioneHCID 21893726Hydrochloride methanolHCID 178418435HCID 178418435, compound

Product 1

HCID 21820315HCID 21820315, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (2.0 g) obtained in step (c) just above was dissolved in methanol (100 ml). Sodium boron hydride (1.7 g) was added to the solution. The mixture was stirred at room temperature for 3 hr. Hydrochloric acid-methanol (50 ml) was added to the reaction solution, and the mixture was stirred at room temperature for one hr. The reaction solution was then extracted with ethyl acetate. The organic layer was 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=1:1) to give 3-methoxy-4,4-dimethyl-3,4-dihydro-2H-isoquinolin-1-one (1.8 g).

Workup

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

Sources & evidence

ORD record
ord-0f6508e444ee4201afa621e0d0898cf7
Source dataset
uspto-grants-2002_07
Patent number
US06417362B1

Reaction notes

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