Phenol → 10H-[1]Benzopyrano[3,2-b]pyridin-10-one

HRID 1731739Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1731739
Cl[C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1C(O)=O.[O-:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C:18]1([OH:24])C=CC=CC=1>O>[N:10]1[C:2]2[C:18](=[O:24])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[O:11][C:3]=2[CH:7]=[CH:8][CH:9]=1

Komponenten

5

Edukt 3

HCID 996PhenolHCID 762582-Chloronicotinic acidHCID 119047Phenolate

Produkt 1

HCID 756683710H-[1]Benzopyrano[3,2-b]pyridin-10-oneAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

According to the invention, 2-chloronicotinic acid in alkaline metal salt form is reacted with alkaline metal phenoxide without an excess of phenol at 160°-200° C. The molten mass is partly cooled, water is added until complete solubilization, the aqueous solution is acidified and the solid obtained is dried. In the cyclization step the thus obtained 2-phenoxynicotinic acid is added portionwise to 5-10 times its weight of polyphosphoric acid which has been previously heated, the temperature is raised to 160°-200° C., the reaction mixture is cooled and diluted with water. Concentrated aqueous alkali hydroxide is added to adjust the pH to 2-3, the solid is filtered, washed, dried and recrystallized, obtaining very pure 1-azaxanthone in an overall yield of 50-70%.

Aufarbeitung

  1. temperatureThe molten mass is partly cooled
  2. customthe solid obtained
  3. customis dried
  4. additionIn the cyclization step the thus obtained 2-phenoxynicotinic acid is added portionwise to 5-10 times its weight of polyphosphoric acid which
  5. temperaturehas been previously heated
  6. temperaturethe temperature is raised to 160°-200° C.
  7. temperaturethe reaction mixture is cooled
  8. additiondiluted with water
  9. additionConcentrated aqueous alkali hydroxide is added
  10. filtrationthe solid is filtered
  11. washwashed
  12. customdried
  13. customrecrystallized

Quellen und Nachweise

ORD-Eintrag
ord-94804006eab741d6a84c502aeb2ae0fd
Quelldatensatz
uspto-grants-1986_11
Patentnummer
US04623648

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