5-Bromo-2-methyl-8-nitro-1,2,3,4-tetrahydroisoquinoline → 5-Bromo-2-methyl-1,2,3,4-tetrahydroisoquinolin-8-amine

HRID 2237385Notes

Reaction equation

HRID 2237385 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([CH3:15])[CH2:7]2>C(O)C.[Ni]>[Br:1][C:2]1[CH:11]=[CH:10][C:9]([NH2:12])=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([CH3:15])[CH2:7]2

Participants

4

Reactant 1

HCID 100160105-Bromo-2-methyl-8-nitro-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 99919145-Bromo-2-methyl-1,2,3,4-tetrahydroisoquinolin-8-amine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of N-methyl-5-bromo-8-nitro-1,2,3,4-tetrahydroisoquinoline (III, 4.7 gm, 17.3 mmol) in ethanol (50 ml), Raney Nickel (solution in water, 1.5 g) was added. The reaction mixture was stirred at room temperature overnight under H2. The mixture was filtered through celite and solvent was removed under vacuum to give IV.

Workup

  1. filtrationThe mixture was filtered through celite and solvent
  2. customwas removed under vacuum

Sources & evidence

ORD record
ord-7c5288c394f14f128e7b45d721e163bd
Source dataset
uspto-grants-2010_05
Patent number
US07718641B2

Reaction notes

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