7-Nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride → 1,2,3,4-Tetrahydroisoquinolin-7-amine

HRID 1808332Notes

Reaction equation

HRID 1808332 reaction equation
Cl.[N+:2]([C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][NH:11][CH2:12]2)=[CH:7][CH:6]=1)([O-])=O>CO.[Pd]>[CH2:12]1[C:13]2[C:8](=[CH:7][CH:6]=[C:5]([NH2:2])[CH:14]=2)[CH2:9][CH2:10][NH:11]1

Participants

4

Reactant 1

HCID 135216707-Nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride

Product 1

HCID 115863231,2,3,4-Tetrahydroisoquinolin-7-amineYield 69.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Pd/C (1.9 g) was added to a solution of 7-nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride (19 g; 1 equiv.) in 300 ml of methanol, and the reaction mixture was hydrogenated for 2 hours at 60 PSI. When the conversion was complete, filtration over Celite was carried out, the filter cake was then washed 4 times with methanol, the filtrate was concentrated under reduced pressure, and the residue was taken up in 100 ml of water. The aqueous solution was adjusted to a pH value of 8-9 with potassium hydroxide solution and extracted 3× with chloroform. The combined organic phases were dried over sodium sulfate and reduced under reduced pressure. 1,2,3,4-Tetrahydroisoquinoline-7-amine (9 g; 69.2%) was obtained in the form of a pale-brown solid.

Workup

  1. filtrationfiltration over Celite
  2. washthe filter cake was then washed 4 times with methanol
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. extractionextracted 3× with chloroform
  5. dry with materialThe combined organic phases were dried over sodium sulfate

Sources & evidence

ORD record
ord-c21e4513acb9488b879e26d17ef83366
Source dataset
uspto-grants-2013_01
Patent number
US08357717B2

Reaction notes

Loading…