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

HRID 1906415Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1906415
[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-b379a5d5837b4336885d52ed2ce0cdca
Quelldatensatz
uspto-grants-1987_03
Patentnummer
US04652564

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