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

HRID 1579447Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1579447
[C:1]([C:3]([C:10]1[CH:11]=[CH:12][C:13]2[O:22][C:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:16]3[C:15](=[O:23])[C:14]=2[CH:24]=1)(C)[C:4]([O:6]CC)=[O:5])#N.Cl>C(O)(=O)C>[O:23]=[C:15]1[C:16]2[C:17](=[N:18][CH:19]=[CH:20][CH:21]=2)[O:22][C:13]2[CH:12]=[CH:11][C:10]([CH:3]([CH3:1])[C:4]([OH:6])=[O:5])=[CH:24][C:14]1=2

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 21568519Ethyl 2-cyano-2-(5-oxo-5H-[1]benzopyrano[2,3-b]pyridin-7-yl)propanoate

Produkt 1

HCID 122741862-(5-oxo-5H-chromeno[2,3-b]pyridin-7-yl)propanoic acidAusbeute 79,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 16.5 g of ethyl 2-cyano-2-(5-oxo-5H-[1]benzopyrano-[2,3-b]pyridin-7-yl)propionate, 80 ml of acetic acid and 35 ml of concentrated hydrochloric acid is heated under reflux for 24 hours. After concentration, water is added to the residue, and further a 10% sodium hydroxide solution is added to dissolve the residue. An insoluble material is removed by extraction with chloroform. The aqueous layer is made acid with acetic acid, and the crystalline precipitate is collected and recrystallized from aqueous dioxane to give 11 g of 2-(5-oxo-5H-[1]benzopyrano[2,3-b]pyridin-7-yl)propionic acid as white needles melting at 194°-195°C.

Aufarbeitung

  1. temperatureis heated
  2. temperatureunder reflux for 24 hours
  3. concentrationAfter concentration, water
  4. additionis added to the residue
  5. additionfurther a 10% sodium hydroxide solution is added
  6. dissolutionto dissolve the residue
  7. customAn insoluble material is removed by extraction with chloroform
  8. customthe crystalline precipitate is collected
  9. customrecrystallized from aqueous dioxane

Quellen und Nachweise

ORD-Eintrag
ord-af16e595e58d40709ffa73c54e7cb429
Quelldatensatz
uspto-grants-1976_01
Patentnummer
US03931205

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