HCID 22758847, compound → HCID 22758843, compound

HRID 1704823Notes

Reaction equation

HRID 1704823 reaction equation
[CH2:1]([CH:4]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH3:15])=[CH:11][CH:12]=2)[C:7]2=[N:16][CH:17]=[C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:19](=[O:20])[N:6]2[CH2:5]1)[CH:2]=[CH2:3]>CC1C=CC(C(C)C)=CC=1.[Pd].C(Cl)Cl>[CH3:15][O:14][C:10]1[CH:9]=[C:8]2[C:13]([C:4]([CH2:1][CH2:2][CH3:3])=[CH:5][N:6]3[C:19](=[O:20])[C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:17][N:16]=[C:7]32)=[CH:12][CH:11]=1

Participants

5

Reactant 1

HCID 22758847HCID 22758847, compound

Product 1

HCID 22758843HCID 22758843, compoundYield 63%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolventHCID 7463P-CymeneSolvent

Procedure

A mixture of ethyl (±)-7-allyl-6,7-dihydro-10-methoxy-4-oxo-4H-pyrimido[2,1-a]isoquinoline-3-carboxylate (190 mgs.) in p-cymene (5 ml.) containing 10% palladium on carbon (50 mgs.) was refluxed for 4 hours. The mixture was cooled, diluted with methylene chloride and filtered to remove the catalyst. The filtrate was evaporated to dryness in vacuo and the residue recrystallized from ethanol, with charcoal treatment, to give yellow needles of title product (119 mgs., 63%), m.p. 187°-188°.

Workup

  1. temperaturewas refluxed for 4 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. customto remove the catalyst
  5. customThe filtrate was evaporated to dryness in vacuo
  6. customthe residue recrystallized from ethanol, with charcoal treatment

Sources & evidence

ORD record
ord-f2642a56af9d47a3b68289eb26cac8e6
Source dataset
uspto-grants-1978_11
Patent number
US04127720

Reaction notes

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