Isoquinolin-5-ol → 1,2,3,4-Tetrahydroisoquinolin-5-ol

HRID 1777177Notes

Reaction equation

HRID 1777177 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>CC(O)=O.O=[Pt]=O>[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]1

Participants

4

Reactant 1

HCID 30386Isoquinolin-5-ol

Product 1

HCID 139482511,2,3,4-Tetrahydroisoquinolin-5-olYield 80%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of isoquinolin-5-ol (4 g, 27.6 mmol) and PtO2 (1.3 g) in HOAc (50 mL) was stirred under H2 (45 Psi) at room temperature overnight. The mixture was filtered and the filtrate was concentrated under vacuum to give the crude product (3.2 g, 80%) which was used in the next step without purification. LCMS (m/z): 150.1 [M+H]+.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-0917d42658ca4b44914cd2fef764d994
Source dataset
uspto-grants-2016_02
Patent number
US09266836B2

Reaction notes

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