Acetic Acid → Acridine-4-carboxylic Acid

HRID 1873069

Reaktionsgleichung

Reaktionsgleichung von HRID 1873069
[CH:1]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:4]([C:15]([O:17]C)=[O:16])=[CH:3][CH:2]=1.[OH-].[Na+].CC(O)=O>C1C2C(=O)C3C(=CC=CC=3)NC=2C=CC=1>[CH:1]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:4]([C:15]([OH:17])=[O:16])=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 11064418Methyl Acridine-4-carboxylate

Produkt 1

HCID 11138739Acridine-4-carboxylic AcidAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2015AcridoneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To methyl acridine-4-carboxylate, prepared in Example 4,(183 mg), was added a degassed solution of NaOH in aqueous EtOH (1:1,2M)(35 ml). The mixture was stirred for 3 hours at 50° C., when a clear solution was obtained, then neutralised with glacial AcOH. Extraction with EtOAc (3×15 50 ml) followed by chromatography on silica gel, eluting with EtOAc/petroleum ether (1:4), gave acridine-4-carboxylic acid (160 mg, 87%), mp (Me2CO) 196-197° C. (lit, mp 202-204° C.).

Aufarbeitung

  1. customwhen a clear solution was obtained
  2. extractionExtraction with EtOAc (3×15 50 ml)
  3. washeluting with EtOAc/petroleum ether (1:4)

Quellen und Nachweise

ORD-Eintrag
ord-3bd7817617e2472e80674c6f20cd3ecd
Quelldatensatz
uspto-grants-2000_08
Patentnummer
US06111109

Verknüpfte Notizen

Wird geladen…