1(2H)-Isoquinolinone → 5,6,7,8-Tetrahydroisoquinolin-1(2H)-one

HRID 1713396

Reaction equation

HRID 1713396 reaction equation
[C:1]1(=[O:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][NH:2]1>C(O)(=O)C.[Pt](=O)=O>[C:1]1(=[O:11])[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][NH:2]1

Participants

4

Reactant 1

HCID 102841(2H)-Isoquinolinone

Product 1

HCID 190811185,6,7,8-Tetrahydroisoquinolin-1(2H)-oneYield 60%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

60 g (413 mmol) of 2H-isoquinolin-1-one (=isocarbostyril) are dissolved in 1 l of glacial acetic acid and, after addition of 2.3 g (10 mmol) of platinum(IV) oxide, hydrogenated under 3 bar at RT until conversion is complete. This entailed changing the catalyst after 3 days and a further 5 days. The suspension is filtered, concentrated and again concentrated after addition of toluene. The crude product is recrystallized from 1.6 l of water. Long needles are filtered off, and the mother liquor is concentrated and dried and separated on silica gel. 36.8 g (60%) of a colorless oil are obtained.

Workup

  1. customat RT
  2. customafter 3 days
  3. customa further 5 days
  4. filtrationThe suspension is filtered
  5. concentrationconcentrated
  6. concentrationagain concentrated
  7. additionafter addition of toluene
  8. customThe crude product is recrystallized from 1.6 l of water
  9. filtrationLong needles are filtered off
  10. concentrationthe mother liquor is concentrated
  11. customdried
  12. customseparated on silica gel

Sources & evidence

ORD record
ord-5a75677ac316463a860bf3df49d0d89c
Source dataset
uspto-grants-2010_09
Patent number
US07795278B2

Linked notes

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