6-nitroisoquinoline-1,3(2H,4H)-dione → 6-Aminoisoquinoline-1,3(2H,4H)-dione

HRID 2236560Notes

Reaction equation

HRID 2236560 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[NH:9][C:8](=[O:15])[CH2:7]2)([O-])=O>CO.CN(C)C=O.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[NH:9][C:8](=[O:15])[CH2:7]2

Participants

5

Reactant 1

HCID 592999676-nitroisoquinoline-1,3(2H,4H)-dione

Product 1

HCID 116224226-Aminoisoquinoline-1,3(2H,4H)-dioneYield 102.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 6.19 g (30 mmol) of 6-nitroisoquinoline-1,3(2H,4H)-dione in 15 ml of MeOH and 150 ml of N,N-DIMETHYLFORMAMIDE is hydrogenated at 1 atmosphere of H2 at 250 in the presence of 1.5 g of 10% Pd/C for 7 h. The catalyst is removed by filtration through Celite. The filtrate is evaporated to give 5.4 g (100%) of a tan solid, mp 200-2200 (dec); MS (ES+) m/z 177.2 (M+H)+1.

Workup

  1. customThe catalyst is removed by filtration through Celite
  2. customThe filtrate is evaporated

Sources & evidence

ORD record
ord-a697de1d28aa4a95a69da15612dd377f
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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