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

HRID 48205Notes

Reaction equation

HRID 48205 reaction equation
Br[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>CO.[Pd]>[CH3:12][N:9]1[CH2:8][CH2:7][C:6]2[C:11](=[CH:2][CH:3]=[C:4]([NH2:14])[C:5]=2[NH2:13])[CH2:10]1

Participants

4

Reactant 1

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

Product 1

HCID 104197311,2,3,4-Tetrahydro-2-methyl-5,6-isoquinolinediamineYield 48.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of the product from Example 10 (1.50 g, 5.24 mmol) and 20% Pd on carbon (0.30 g) in 100 mL of MeOH was hydrogenated at room temperature and pressure for 24 hours. The reaction mixture was filtered and the filtrate concentrated. The residue was partitioned between CHCl3 and saturated aqueous NaHCO3 solution. The organic phase was separated and the aqueous phase was extracted with additional CHCl3 and the combined organic extracts were dried (Na2SO4), filtered, and concentrated. The residue was filtered through a plug of silica gel eluting with 25% EtOH/EtOAc. The eluant was concentrated to give the title compound as an oil (0.45 g, 48%).

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate concentrated
  4. customThe residue was partitioned between CHCl3 and saturated aqueous NaHCO3 solution
  5. customThe organic phase was separated
  6. extractionthe aqueous phase was extracted with additional CHCl3
  7. dry with materialthe combined organic extracts were dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. filtrationThe residue was filtered through a plug of silica gel eluting with 25% EtOH/EtOAc
  11. concentrationThe eluant was concentrated

Sources & evidence

ORD record
ord-b576187f356f4ac0a5116c77df25f56f
Source dataset
uspto-grants-2004_03
Patent number
US06703391B2

Reaction notes

Loading…