8-Bromo-1,2,3,4-tetrahydro-2-methyl-6-nitro-5-isoquinolinamine → 8-Bromo-1,2,3,4-tetrahydro-2-methyl-5,6-isoquinolinediamine

HRID 48204Notes

Reaction equation

HRID 48204 reaction equation
[Br:1][C:2]1[C:11]2[CH2:10][N:9]([CH3:12])[CH2:8][CH2:7][C:6]=2[C:5]([NH2:13])=[C:4]([N+:14]([O-])=O)[CH:3]=1>C1COCC1.[Ni]>[Br:1][C:2]1[CH:3]=[C:4]([NH2:14])[C:5]([NH2:13])=[C:6]2[C:11]=1[CH2:10][N:9]([CH3:12])[CH2:8][CH2:7]2

Participants

4

Reactant 1

HCID 100168198-Bromo-1,2,3,4-tetrahydro-2-methyl-6-nitro-5-isoquinolinamine

Product 1

HCID 103550328-Bromo-1,2,3,4-tetrahydro-2-methyl-5,6-isoquinolinediamineYield 90.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product from Example 10 (0.78 g, 2.73 mmol) in 100 mL of THF was treated with Raney nickel (1.0 g) and hydrogenated for 1.5 hours at room temperature. The reaction mixture was filtered and concentrated to give the title compound as a tan solid (0.63 g, 90%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-173703b7c60b4c998a0161a33606f342
Source dataset
uspto-grants-2004_03
Patent number
US06703391B2

Reaction notes

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