2,4,4-Trimethyl-7-nitroisoquinoline-1,3(2H,4H)-dione → HCID 18382709, compound

HRID 650946Notes

Reaction equation

HRID 650946 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([C:8]([CH3:18])([CH3:17])[C:9](=[O:16])[N:10]([CH3:15])[C:11]2=[O:14])=[CH:6][CH:5]=1)([O-])=O>CO.ClCCl.[Pd]>[NH2:1][C:4]1[CH:13]=[C:12]2[C:7]([C:8]([CH3:18])([CH3:17])[C:9](=[O:16])[N:10]([CH3:15])[C:11]2=[O:14])=[CH:6][CH:5]=1

Participants

5

Reactant 1

HCID 183826212,4,4-Trimethyl-7-nitroisoquinoline-1,3(2H,4H)-dione

Product 1

HCID 18382709HCID 18382709, compoundYield 100.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

7-Nitro-2,4,4-trimethyl-4H-isoquinoline-1,3-dione (45 g, 20 mmol) was dissolved in a methanol (500 ml)/dichloromethane (100 ml) mixture and treated with 10% Pd/C (0.5 g). The reaction mixture was hydrogenated for 2 h before removal of the palladium catalyst by filtration through Celite. The filtrate was evaporated to dryness in vacuo to give the title compound (4.4 g, quant).

Workup

  1. customThe reaction mixture was hydrogenated for 2 h before removal of the palladium catalyst by filtration through Celite
  2. customThe filtrate was evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-ebbedc0c738949feaacb99a3d2e5c667
Source dataset
uspto-grants-2001_08
Patent number
US06277861B1

Reaction notes

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