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

HRID 48203Notes

Reaction equation

HRID 48203 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:17]([O-:19])=[O:18])[C:5]([NH:13]C(=O)C)=[C:6]2[C:11]=1[CH2:10][N:9]([CH3:12])[CH2:8][CH2:7]2.[NH4+].[OH-]>O>[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+:17]([O-:19])=[O:18])[CH:3]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 10065054N-(8-bromo-1,2,3,4-tetrahydro-2-methyl-6-nitro-5-isoquinolinyl)acetamide

Product 1

HCID 100168198-Bromo-1,2,3,4-tetrahydro-2-methyl-6-nitro-5-isoquinolinamineYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of the product from Example 7 (3.68 g, 11.2 mmol) and 80 mL of 3:2H2SO4:H2O was heated at 90° C. for 1 hour. The reaction mixture was cooled and poured onto ice, and the resulting solution was made basic with concentrated aqueous NH4OH solution. The solid that formed was collected by suction filtration and dried under vacuum to give the title compound as a yellow solid (3.17 g, 99%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. additionpoured onto ice
  3. customThe solid that formed
  4. filtrationwas collected by suction filtration
  5. customdried under vacuum

Sources & evidence

ORD record
ord-cbb1d9bde2784addb419500705adbb72
Source dataset
uspto-grants-2004_03
Patent number
US06703391B2

Reaction notes

Loading…