Hydrochloric Acid → 9-Amino-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline

HRID 583295Notes

Reaction equation

HRID 583295 reaction equation
Cl.[N+:2]([C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][N:11]3[CH2:17][CH2:16][CH2:15][CH:12]32)=[CH:7][CH:6]=1)([O-])=O.Cl.[H][H]>CO.[Pd]>[NH2:2][C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][N:11]3[CH2:17][CH2:16][CH2:15][CH:12]32)=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 215842749-Nitro-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline hydrochlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 114354049-Amino-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinolineYield 104.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 9-nitro-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline hydrochloride (Example 31(b), 2.0 g) in methanol (100 ml) was added concentrated hydrochloric acid (0.67 ml) and 5% palladium on carbon (200 mg). The mixture was hydrogenated at 50 psi on a Parr Hydrogenator. Hydrogen uptake was complete in 1.0 h. The catalyst was filtered off and the solvent removed under reduced pressure. The residue was dissolved in water, the solution basified with 2.5M sodium hydroxide and the product extracted into dichloromethane. The extracts were dried over anhydrous magnesium sulfate and the solvent removed under reduced pressure to yield the title compound as a thick oil (1.55 g).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent removed under reduced pressure
  3. dissolutionThe residue was dissolved in water
  4. extractionthe product extracted into dichloromethane
  5. dry with materialThe extracts were dried over anhydrous magnesium sulfate
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-abf4764360234e0793555c7672a8fe4f
Source dataset
uspto-grants-1999_07
Patent number
US05929085

Reaction notes

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