Sodium Hydroxide → 2-(5-oxo-5H-chromeno[2,3-b]pyridin-7-yl)propanoic acid

HRID 1579453Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1579453
Cl[C:2]1[N:21]=[CH:20][CH:19]=[CH:18][C:3]=1[C:4]([C:6]1[CH:7]=[C:8]([CH:13]([CH3:17])[C:14]([OH:16])=[O:15])[CH:9]=[CH:10][C:11]=1[OH:12])=[O:5].[OH-].[Na+]>O.[Cu].[Cu](I)I>[O:5]=[C:4]1[C:3]2[C:2](=[N:21][CH:20]=[CH:19][CH:18]=2)[O:12][C:11]2[CH:10]=[CH:9][C:8]([CH:13]([CH3:17])[C:14]([OH:16])=[O:15])=[CH:7][C:6]1=2

Komponenten

6

Edukt 2

HCID 14798Sodium HydroxideHCID 215685182-[3-(2-Chloronicotinoyl)-4-hydroxyphenyl]propionic acid

Produkt 1

HCID 122741862-(5-oxo-5H-chromeno[2,3-b]pyridin-7-yl)propanoic acidAusbeute 72,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23978CopperKatalysatorHCID 83717Copper iodideKatalysatorHCID 962WaterLösungsmittel2×

Versuchsvorschrift

2.5 g of 2-[3-(2-chloronicotinoyl)-4-hydroxyphenyl]propionic acid and 0.7 g of sodium hydroxide are dissolved in 10 ml of water. Catalytic amounts of powdered copper and copper iodide are added to the solution, and the mixture is stirred under reflux for 2 hours. After cooling, the reaction mixture is diluted with water, and filtered with suction. The filtrate is made acid with hydrochloric acid, and the resulting crystals are filtered off and recrystallized from aqueous dioxane to give 1.6 g of 2-(5-oxo-5H-[1]benzopyrano[2,3-b]pyridin-7-yl)propionic acid melting at 193.5°-194.5°C.

Aufarbeitung

  1. temperatureunder reflux for 2 hours
  2. temperatureAfter cooling
  3. filtrationfiltered with suction
  4. filtrationthe resulting crystals are filtered off
  5. customrecrystallized from aqueous dioxane

Quellen und Nachweise

ORD-Eintrag
ord-aba23d85e11448cd8658ea3309c72a6e
Quelldatensatz
uspto-grants-1976_01
Patentnummer
US03931205

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