Ethyl 4-Oxo-4H-pyrimido[2,1-a]isoquinoline-3-carboxylate → Ethyl 6,7-Dihydro-4-oxo-4H-pyrimido[2,1-a]isoquinoline-3-carboxylate

HRID 1704817Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1704817
[O:1]=[C:2]1[N:7]2[CH:8]=[CH:9][C:10]3[C:15]([C:6]2=[N:5][CH:4]=[C:3]1[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][CH:13]=[CH:12][CH:11]=3.[H][H]>C(O)(=O)C.[Pd]>[O:1]=[C:2]1[N:7]2[CH2:8][CH2:9][C:10]3[C:15]([C:6]2=[N:5][CH:4]=[C:3]1[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][CH:13]=[CH:12][CH:11]=3

Komponenten

5

Edukt 2

HCID 13851097Ethyl 4-Oxo-4H-pyrimido[2,1-a]isoquinoline-3-carboxylateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 22758857Ethyl 6,7-Dihydro-4-oxo-4H-pyrimido[2,1-a]isoquinoline-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of ethyl 4-oxo-4H-pyrimido[2,1-a]isoquinoline-3-carboxylate (2.68 g., 0.010 mole) in acetic acid (200 ml.) containing 10% palladium on carbon (1.0 g.) was shaken with hydrogen at an initial pressure of about 4 kg. cm.-2 until the theoretical pressure drop was reached (3.3 hours). The mixture was filtered and the filtrate flash evaporated to dryness to leave an oil, which upon dilution with toluene and reconcentration to dryness gave colorless crystalline material, m.p. 117°-125°. Two recrystallizations from ethanol raised the m.p. to 139°-141°. This material was combined with product of similar purity which separated from the first ethanolic mother liquor, and the lot recrystallized from cyclohexane to give the analytical sample, m.p. 138.5°-140°.

Aufarbeitung

  1. custom(3.3 hours)
  2. filtrationThe mixture was filtered
  3. customthe filtrate flash evaporated to dryness
  4. customto leave an oil, which upon dilution with toluene and reconcentration to dryness
  5. customgave colorless crystalline material, m.p. 117°-125°
  6. customTwo recrystallizations from ethanol
  7. temperatureraised the m.p. to 139°-141°
  8. customseparated from the first ethanolic mother liquor
  9. customthe lot recrystallized from cyclohexane
  10. customto give the analytical sample, m.p. 138.5°-140°

Quellen und Nachweise

ORD-Eintrag
ord-f46a86c92afc4f09b3c8cd68b93c6d47
Quelldatensatz
uspto-grants-1978_11
Patentnummer
US04127720

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