HCID 22758830, compound → HCID 22758826, compound

HRID 1704821Notes

Reaction equation

HRID 1704821 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]1=[N:13][CH:14]=[C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:16](=[O:17])[N:8]1[CH2:7][CH2:6]2>CC1C=CC(C(C)C)=CC=1.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]1=[N:13][CH:14]=[C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:16](=[O:17])[N:8]1[CH:7]=[CH:6]2

Participants

4

Reactant 1

HCID 22758830HCID 22758830, compound

Product 1

HCID 22758826HCID 22758826, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7463P-CymeneSolvent

Procedure

A stirred mixture of ethyl 6,7-dihydro-9-methoxy-4-oxo-4H-pyrimido[2,1-a]isoquinoline-3-carboxylate (510 mgs.) in p-cymene (25 ml.) containing 10% palladium on carbon (150 mgs.) was refluxed for 7 hours. The mixture was flash evaporated to dryness and the residue extracted with boiling ethanol. The combined extracts were filtered and concentrated by boiling to give flocculent colorless needles of ethyl 9-methoxy-4-oxo-4H-pyrimido[2,1-a]isoquinoline-3-carboxylate: 420 mgs. (81% yield), m.p. 211.5°-212°. An additional recrystallization from ethanol raised the m.p. to 217°-218°.

Workup

  1. temperaturewas refluxed for 7 hours
  2. customevaporated to dryness
  3. extractionthe residue extracted with boiling ethanol
  4. filtrationThe combined extracts were filtered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d181e71b46ce4dc7b3cb2dc7c4d85d92
Source dataset
uspto-grants-1978_11
Patent number
US04127720

Reaction notes

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