Isoquinolin-5-ol → 1,2,3,4-Tetrahydroisoquinolin-5-ol
Reaction equation
[CH:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([OH:11])[C:5]=2[CH:4]=[CH:3][N:2]=1>C(O)(=O)C>[CH2:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([OH:11])[C:5]=2[CH2:4][CH2:3][NH:2]1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
Isoquinolin-5-ol (Aldrich, Cat. #H33207)(0.75 g, 5.2 mmol) was dissolved in acetic acid (20.0 mL) in a Parr shaker bottle. The reaction was degassed with nitrogen, and the platinum dioxide (0.050 g) was added. The reaction was charged to 55 Psi hydrogen and shaken. After shaking for 24 h. the reaction was complete. This was filtered to remove the catalyst and concentrated under reduced pressure give a dark amber 1,2,3,4-tetrahydroisoquinolin-5-ol (0.70 g, 90%) as an oil. Analytical LCMS (M+H)+: m/z=150.1.
Workup
- customThe reaction was degassed with nitrogen
- additionthe platinum dioxide (0.050 g) was added
- additionThe reaction was charged to 55 Psi hydrogen
- stirringAfter shaking for 24 h. the reaction
- filtrationThis was filtered
- customto remove the catalyst
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-57265a60d78f4d2fae3da2db3afff653
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08481732B2
Reaction notes
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