5-Bromo-1,2,3,4-tetrahydro-7-nitro-2-(3-phenylpropyl)-8-isoquinolinamine → 5-Bromo-1,2,3,4-tetrahydro-2-(3-phenylpropyl)-7,8-isoquinolinediamine

HRID 1106431Notes

Reaction equation

HRID 1106431 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]([CH2:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[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]([CH2:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:7]2

Participants

4

Reactant 1

HCID 155241945-Bromo-1,2,3,4-tetrahydro-7-nitro-2-(3-phenylpropyl)-8-isoquinolinamine

Product 1

HCID 155241955-Bromo-1,2,3,4-tetrahydro-2-(3-phenylpropyl)-7,8-isoquinolinediamineYield 96.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product from Example 12 (1.1 g, 2.82 mmol) in THF (80 mL) was stirred over RaNi under a hydrogen balloon for 19 hours. The catalyst was filtered off and concentrated under vacuum to give the title compound (0.98 g, 96% yield) as a dark brown oil.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b217f0577198428798e98c5e9351526e
Source dataset
uspto-grants-2000_05
Patent number
US06057313

Reaction notes

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