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

HRID 2297604Notes

Reaction equation

HRID 2297604 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-trimethyl4H-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). 1H NMR (250 MHz, CDCl3)≃:1.58 (6H, s), 3.36 (3H, s), 3.83 (2H, brs), 6.95 (1H, dd, J=6, 3 Hz), 7.24 (1H, d, J=6 Hz), 7.48 (1H, d, J=3 Hz); m/z (API+): 219 (M+H)+

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-5e89ebe34a864aecb81f07625d6712dc
Source dataset
uspto-grants-2002_12
Patent number
US06492378B1

Reaction notes

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