5-Aminoisoquinoline → 5-Amino-1,2,3,4-tetrahydroisoquinoline

HRID 1194100

Reaction equation

HRID 1194100 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.[H][H]>C(O)(=O)C.[Pt]=O>[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][NH:6][CH2:7]2

Participants

5

Reactant 2

HCID 707665-AminoisoquinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 162174995-Amino-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 5-aminoisoquinoline (20 g) in glacial acetic acid (500 ml) was shaken under hydrogen in the presence of a platinum oxide catalyst (2.0 g) at room temperature and approximately 345 kilopascals pressure until uptake of hydrogen stopped. The catalyst was removed by filtration and the filtrate was evaporated to a small volume under reduced pressure. Residual solvent was removed by co-evaporation with water, then isopropyl alcohol, and the resulting solid was recrystallized from isopropyl alcohol to give 5-amino-1,2,3,4-tetrahydroisoquinoline as a white solid, 19 g, m.p. 153°-154° C.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated to a small volume under reduced pressure
  3. customResidual solvent was removed by co-evaporation with water
  4. customisopropyl alcohol, and the resulting solid was recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-8186bc04f14c47bcbe302433515f8a22
Source dataset
uspto-grants-1989_03
Patent number
US04812573

Linked notes

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