3-Methyl-1,2-dihydroisoquinolin-1-one → 3-Methyl-5,6,7,8-tetrahydro-2H-isoquinolin-1-one

HRID 1713395Notes

Reaction equation

HRID 1713395 reaction equation
[CH3:1][C:2]1[NH:3][C:4](=[O:12])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2>C(O)(=O)C.[Pt](=O)=O>[CH3:1][C:2]1[NH:3][C:4](=[O:12])[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1

Participants

4

Reactant 1

HCID 32444773-Methyl-1,2-dihydroisoquinolin-1-one

Product 1

HCID 123314983-Methyl-5,6,7,8-tetrahydro-2H-isoquinolin-1-oneYield 83%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

8.45 g (53 mmol) of 3-methyl-2H-isoquinolin-1-one are dissolved in 80 ml of glacial acetic acid and, after addition of 168 mg (0.74 mmol) of platinum(IV) oxide, hydrogenated under 5 bar at RT for 8 h. The suspension is filtered and concentrated and the residue is recrystallized from methanol. 7.15 g (83%) of a colorless oil are obtained.

Workup

  1. filtrationThe suspension is filtered
  2. concentrationconcentrated
  3. customthe residue is recrystallized from methanol

Sources & evidence

ORD record
ord-a89b661876994b46a6e0d2618adf0d8c
Source dataset
uspto-grants-2010_09
Patent number
US07795278B2

Reaction notes

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