4a-Phenyl-4a,5,6,7-tetrahydroisoquinoline-1,3(2H,4H)-dione → HCID 86736479, compound

HRID 26476Notes

Reaction equation

HRID 26476 reaction equation
[C:1]1([C:7]23[CH2:16][CH2:15][CH2:14][CH:13]=[C:12]2[C:11](=[O:17])[NH:10][C:9](=[O:18])[CH2:8]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>C(O)(=O)C.O1CCOCC1.[Pd]>[C:1]1([C@@:7]23[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2[C:11](=[O:17])[NH:10][C:9](=[O:18])[CH2:8]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 132819694a-Phenyl-4a,5,6,7-tetrahydroisoquinoline-1,3(2H,4H)-dioneHCID 178418361HCID 178418361, compound

Product 1

HCID 86736479HCID 86736479, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

4a-Phenyl-1,3-diketo-1,2,3,4,4a,5,6,7-octahydroisoquinoline (3.0 g, 12.45 mmoles) from Ex. 1B was dissolved in 100 ml of glacial acetic acid and 50 ml of dioxane. The catalyst, 5% palladium on carbon (700 mg), was added and the mixture was hydrogenated under 40 psi of hydrogen for 24 hours in a Parr shaker. The catalyst was then filtered off and the filtrate evaporated. The white crystalline 4a-phenyl-1,3-diketo-trans-decahydroisoquinoline was recrystallized from ethanol, mp 180°-182.5°.

Workup

  1. filtrationThe catalyst was then filtered off
  2. customthe filtrate evaporated
  3. customThe white crystalline 4a-phenyl-1,3-diketo-trans-decahydroisoquinoline was recrystallized from ethanol, mp 180°-182.5°

Sources & evidence

ORD record
ord-036fb69926a9475f9e90660da74225b3
Source dataset
uspto-grants-1979_04
Patent number
US04150135

Reaction notes

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