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

HRID 1370570Notes

Reaction equation

HRID 1370570 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-3098e39ddeac49af93db50d55e508841
Source dataset
uspto-grants-2003_06
Patent number
US06583144B2

Reaction notes

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