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Formamidine acetate → Medorinone

HRID 462718
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 462718
[C:1]([C:4]1[CH:5]=[CH:6][C:7](=[O:15])[NH:8][C:9]=1[CH:10]=[CH:11][N:12](C)C)(=O)[CH3:2].C(O)(=O)C.C(N)=N>CN(C)C=O>[CH3:2][C:1]1[N:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7](=[O:15])[NH:8]2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 160693Formamidine acetateHCID 37350622(1H)-Pyridinone, 5-acetyl-6-[2-(dimethylamino)ethenyl]-

Produkt 1

HCID 5362132MedorinoneAusbeute 83,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

E-7b. 5-Methyl-1,6-naphthyridin-2(1H)-one--A mixture containing 10.3 g of 5-acetyl-6-(2-dimethylaminoethenyl)-2(1H)-pyridinone, 10.4 g of formamidine acetate and 75 ml of dimethylformamide was heated on a steam bath for 5 hours and then concentrated to dryness on a rotary evaporator. The residue was treated with 50 ml of water and again stripped to dryness The white residue was recrystallized from isopropyl alcohol to yield 6.7 g of 5-methyl-1,6-naphthyridin-2(1H)-one, m.p. 238°-240° C. This compound was the same as the compound of Example E-7a, e.g., a mixed melting point showed no depression and the infrared and nuclear magnetic resonance spectral data for the compounds were respectively the same.

Aufarbeitung

  1. temperaturewas heated on a steam bath for 5 hours
  2. concentrationconcentrated to dryness on a rotary evaporator
  3. additionThe residue was treated with 50 ml of water
  4. customwas recrystallized from isopropyl alcohol

Quellen und Nachweise

ORD-Eintrag
ord-2d985cc492714e95aed1d1a50a1a4298
Quelldatensatz
uspto-grants-1985_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04517190

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