Isoquinoline → 1,2,3,4-Tetrahydroisoquinoline

HRID 542255Notes

Reaction equation

HRID 542255 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1>[Ni]>[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1

Participants

3

Reactant 1

HCID 8405Isoquinoline

Product 1

HCID 70461,2,3,4-TetrahydroisoquinolineYield 88.9%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

In an autoclave, 1.2 kg of the same crude isoquinoline as used in Example 2 and 180 g of the aforementioned stabilized nickel catalyst were subjected to hydrogenation at a temperature of 180° C. under a hydrogen pressure of 135 kg/cm2 ·G for 65 hours. The amount of hydrogen absorbed was 29.9 moles and the molar ratio of the hydrogen absorption (by molar ratio based on raw material) was 3.22. The resultant reaction mixture was separated by filtration and then distilled. Consequently, 1.1 kg of 1,2,3,4-tetrahydroisoquinoline (purity 94.6% and total sulfur content 0%) was obtained.

Workup

  1. customwere subjected to hydrogenation at a temperature of 180° C. under a hydrogen
  2. custom·G for 65 hours
  3. customThe amount of hydrogen absorbed
  4. customthe molar ratio of the hydrogen absorption (by molar ratio based on raw material)
  5. customThe resultant reaction mixture
  6. customwas separated by filtration
  7. distillationdistilled

Sources & evidence

ORD record
ord-7d2fcae834414187ba19235ee2420fe2
Source dataset
uspto-grants-1987_04
Patent number
US04656279

Reaction notes

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