5-Bromo-1,2,3,4-tetrahydro-2-methyl-7-nitro-8-isoquinolinamine → 5-Bromo-1,2,3,4-tetrahydro-2-methyl-7,8-isoquinolinediamine

HRID 48222Notes

Reaction equation

HRID 48222 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]([N+:12]([O-])=O)[C:9]([NH2:15])=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([CH3:16])[CH2:7]2>C1COCC1.[Ni]>[Br:1][C:2]1[CH:11]=[C:10]([NH2:12])[C:9]([NH2:15])=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([CH3:16])[CH2:7]2

Participants

4

Reactant 1

HCID 104466755-Bromo-1,2,3,4-tetrahydro-2-methyl-7-nitro-8-isoquinolinamine

Product 1

HCID 104225225-Bromo-1,2,3,4-tetrahydro-2-methyl-7,8-isoquinolinediamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product from Example 60 (1.02 g, 3.49 mmol) in 50 mL THF was treated with Raney nickel (prewashed with acetone followed by THF), and the reaction vessel was purged with H2. After stirring for 2.5 hours, the catalyst was removed by filtration and the filtrate evaporated to give a tan oil. The product was used without further purification.

Workup

  1. customthe reaction vessel was purged with H2
  2. customthe catalyst was removed by filtration
  3. customthe filtrate evaporated
  4. customto give a tan oil
  5. customThe product was used without further purification

Sources & evidence

ORD record
ord-c8ab3f5e8e5a4aebae8cd41a5c2b99fd
Source dataset
uspto-grants-2004_03
Patent number
US06703391B2

Reaction notes

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