Gamma-Butyrolactone → 4-hydroxy-3-(2-hydroxyethyl)-1-phenyl-1,8-naphthyridin-2(1H)-one

HRID 2118692Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2118692
[C:1]1([NH:7][C:8]2[C:13]([C:14]([O:16]C)=O)=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18]1(=[O:23])[O:22][CH2:21][CH2:20][CH2:19]1.CC(C)([O-])C.[K+]>>[OH:23][CH2:18][CH2:19][C:20]1[C:21](=[O:22])[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[C:13]([C:14]=1[OH:16])=[CH:12][CH:11]=[CH:10][N:9]=2

Komponenten

4

Edukt 3

HCID 7302Gamma-ButyrolactoneHCID 10998755Methyl 2-anilinopyridine-3-carboxylateHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 547236674-hydroxy-3-(2-hydroxyethyl)-1-phenyl-1,8-naphthyridin-2(1H)-one

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

To a solution of 6.8 g. of methyl 2-phenylamino-3-pyridine carboxylate in 60 ml. of gamma-butyrolactone there was added, under nitrogen, 13.4 g. of potassium tertiary butoxide. The reaction mixture was heated and stirred for one hour at 95° C., poured on ice and stirred overnight. The mixture was extracted with ether, the aqueous layer acidified with acetic acid to pH 4.5 and the product was collected by filtration. Recrystallization from chloroform, acetone, isopropanol yielded the product of this example as a colorless solid; m.p. 235°-236° C.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. additionpoured on ice
  3. stirringstirred overnight
  4. extractionThe mixture was extracted with ether
  5. filtrationthe product was collected by filtration
  6. customRecrystallization from chloroform, acetone, isopropanol
  7. customyielded the product of this example as a colorless solid

Quellen und Nachweise

ORD-Eintrag
ord-b2581a841d5842159e76aecfd7627c0f
Quelldatensatz
uspto-grants-1987_07
Patentnummer
US04680297

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