5-Bromo-2-methyl-8-nitro-1,2,3,4-tetrahydroisoquinoline → 5-Bromo-2-methyl-1,2,3,4-tetrahydroisoquinolin-8-amine
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]2Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
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
- filtrationThe mixture was filtered through celite and solvent
- 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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