Reaction #76483

Reaction equation

product

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

→

title compound

Yield 48.5%

1,2,3,4-Tetrahydro-2-methyl-5,6-isoquinolinediamine

Yield 48.5%

Solvents

MeOH

Conditions

Workup

1. 1
   Otherwas hydrogenated at room temperature
2. 2
   FiltrationThe reaction mixture was filtered
3. 3
   Concentrationthe filtrate concentrated
4. 4
   OtherThe residue was partitioned between CHCl3 and saturated aqueous NaHCO3 solution
5. 5
   OtherThe organic phase was separated
6. 6
   Extractionthe aqueous phase was extracted with additional CHCl3
7. 7
   Dryingthe combined organic extracts were dried (Na2SO4)
8. 8
   Filtrationfiltered
9. 9
   Concentrationconcentrated
10. 10
    FiltrationThe residue was filtered through a plug of silica gel eluting with 25% EtOH/EtOAc
11. 11
    ConcentrationThe eluant was concentrated

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%).

Source