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Hydrochloric Acid → 7-acetyl-2-amino-5-oxo-5H-chromeno[2,3-b]pyridine-3-carboxylic acid

HRID 986762
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 986762
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:22][C:11]3=[N:12][C:13]([NH2:21])=[C:14]([C:16]([O:18]CC)=[O:17])[CH:15]=[C:10]3[C:9](=[O:23])[C:8]=2[CH:24]=1)(=[O:3])[CH3:2].[OH-].[Na+].Cl>C(O)C.O>[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:22][C:11]3=[N:12][C:13]([NH2:21])=[C:14]([C:16]([OH:18])=[O:17])[CH:15]=[C:10]3[C:9](=[O:23])[C:8]=2[CH:24]=1)(=[O:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13728611HCID 13728611, Verbindung

Produkt 1

HCID 137286127-acetyl-2-amino-5-oxo-5H-chromeno[2,3-b]pyridine-3-carboxylic acidAusbeute 93,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel
HCID 962
Water
Lösungsmittel
2×

Versuchsvorschrift

In ethanol (3 l) was suspended ethyl 7-acetyl-2-amino-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine-3-carboxylate (46 g). To the suspension were added water (460 ml) and 1N sodium hydroxide (462 ml). The mixture was stirred at room temperature for 1.5 hour, then at 50°-55° C. for 2 hours. The precipitating crystals were collected by filtration, and washed with ethanol. The crystals thus obtained were suspended in warm water (about 2 l). To the suspension was added concentrated hydrochloric acid (20 ml), and the mixture was stirred for 20 minutes. Insoluble matter was collected by filtration, washed with water, followed by recrystallization from dimethylformamide-water to give 7-acetyl-2-amino-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine-3-carboxylic acid as colorless crystals (39.3 g). Melting point: >300° C.

Aufarbeitung

  1. waitat 50°-55° C. for 2 hours
  2. filtrationThe precipitating crystals were collected by filtration
  3. washwashed with ethanol
  4. customThe crystals thus obtained
  5. stirringthe mixture was stirred for 20 minutes
  6. filtrationInsoluble matter was collected by filtration
  7. washwashed with water
  8. customfollowed by recrystallization from dimethylformamide-water

Quellen und Nachweise

ORD-Eintrag
ord-e315e9a42d544c98937e7404ad3dcafe
Quelldatensatz
uspto-grants-1987_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04716167

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