5-Nitroisoquinoline → 5-Aminoisoquinoline

HRID 2397922Notes

Reaction equation

HRID 2397922 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][N:8]=[CH:9]2)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][N:8]=[CH:9]2

Participants

4

Reactant 1

HCID 690855-Nitroisoquinoline

Product 1

HCID 707665-AminoisoquinolineYield 112%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5-Nitroisoquinoline (16.4 g) was dissolved in methanol (200 ml) and hydrogenated over palladium on charcoal (1.64 g) at 45 psi. When the hydrogenation was complete, the catalyst was removed by filtration and the solvent removed in vacuo to yield 15.2 g of 5-aminoisoquinoline as a brown powder. This was recrystallized from chloroform-ligroin (b.p. 60°-90° C.) to yield 5-aminoisoquinoline (12.1 g) as a light tan powder, m.p. 127°-129° C. (lit. value, 128° C.).

Workup

  1. customthe catalyst was removed by filtration
  2. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-c3a8a631f81b411d94da641b0412f574
Source dataset
uspto-grants-1977_05
Patent number
US04022900

Reaction notes

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