5-Nitroisoquinoline → 5-Aminoisoquinoline

HRID 48219

Reaction equation

HRID 48219 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.[Ni]>[CH:9]1[C:10]2[CH:11]=[CH:12][CH:13]=[C:4]([NH2:1])[C:5]=2[CH:6]=[CH:7][N:8]=1

Participants

4

Reactant 1

HCID 690855-Nitroisoquinoline

Product 1

HCID 707665-AminoisoquinolineYield 98%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

5-Nitroisoquinoline (100.3 g, 0.576 mol) was dissolved in MeOH and shaken with Raney nickel (10 g) on a Parr apparatus under a H2 atmosphere (50 psi) for 21 hours. The MeOH was removed in vacuo, the residue dissolved in chloroform (150 mL), and filtered into 600 mL petroleum ether. The solid was collected by filtration. This trituration procedure was repeated several times to give 81.24 g (98%) of the desired product.

Workup

  1. customThe MeOH was removed in vacuo
  2. dissolutionthe residue dissolved in chloroform (150 mL)
  3. filtrationfiltered into 600 mL petroleum ether
  4. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-acd1c103d3db423b8f7a7621644f9507
Source dataset
uspto-grants-2004_03
Patent number
US06703391B2

Linked notes

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