N-ethyl-5-bromo-8-nitrotetrahydroisoquinoline → N-ethyl-5-bromo-8-aminotetrahydroisoquinoline

HRID 48210Notes

Reaction equation

HRID 48210 reaction equation
[CH2:1]([N:3]1[CH2:12][CH2:11][CH:10]2[C:5](=[C:6]([N+:14]([O-])=O)[CH:7]=[CH:8][CH:9]2[Br:13])[CH2:4]1)[CH3:2].[H][H]>[Ni].CC(C)=O.C1COCC1>[CH2:1]([N:3]1[CH2:12][CH2:11][CH:10]2[C:5](=[C:6]([NH2:14])[CH:7]=[CH:8][CH:9]2[Br:13])[CH2:4]1)[CH3:2]

Participants

6

Reactant 2

HCID 69895026N-ethyl-5-bromo-8-nitrotetrahydroisoquinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 69894940N-ethyl-5-bromo-8-aminotetrahydroisoquinoline

Reagents, catalysts & solvents 3

HCID 935NickelCatalyst2×HCID 180AcetoneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Raney nickel was refluxed in acetone for 2 hours prior to use to deactivate the metal. The product from Example 26 (0.1 g, 0.35 mmol) was dissolved in THF (10 mL), the Raney nickel added, and the reaction vessel charged with hydrogen gas. After stirring for 1 hour, the Raney nickel was removed by filtration and the solvent removed by filtration to give N-ethyl-5-bromo-8-aminotetrahydroisoquinoline (used without further purification).

Workup

  1. customthe Raney nickel was removed by filtration
  2. customthe solvent removed by filtration

Sources & evidence

ORD record
ord-88d85bad3d2548ecb739e754cda72ea3
Source dataset
uspto-grants-2004_03
Patent number
US06703391B2

Reaction notes

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