Naphthalic anhydride → N-Hydroxynaphthalimide

HRID 6613

Reaktionsgleichung

Reaktionsgleichung von HRID 6613
Cl.[NH2:2][OH:3].[C:4]12[C:17](=[O:18])O[C:14](=[O:15])[C:12]3=[C:13]1[C:8](=[CH:9][CH:10]=[CH:11]3)[CH:7]=[CH:6][CH:5]=2>N1C=CC=CC=1>[CH:6]1[CH:5]=[C:4]2[C:17]([N:2]([OH:3])[C:14]([C:12]3=[CH:11][CH:10]=[CH:9][C:8](=[C:13]23)[CH:7]=1)=[O:15])=[O:18]

Komponenten

4

Edukt 2

HCID 6693Naphthalic anhydrideHCID 443297Hydroxyamine hydrochloride

Produkt 1

HCID 82263N-HydroxynaphthalimideAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A 3-L flask equipped with a stirrer, cooling tube and thermometer was purged by nitrogen gas. 55.2 g (770 mmol) of hydroxylamine-hydrochloride (purity of 97%) and 1.2 L of pyridine were added to the flask and were stirred to dissolve at room temperature under nitrogen atmosphere. To the stirred mixture, 138.7 g (700 mmol) of 1,8-naphthalenedicarboxylic anhydride was added. The stirred mixture was heated at 40° C. for 1 hour and subsequently was heated at 70° C. for 1 hour. After stirring at 90° C. for 1 hour, the reaction mixture was cooled to room temperature with stirring. The resulting crystalline solid was filtered off and washed with 5% by weight of acetic acid aqueous solution and dried at 80° C. for 20 hours under a reduced pressure to yield 120.7 g (81%) of N-hydroxynaphthalimide with yellow color.

Aufarbeitung

  1. customA 3-L flask equipped with a stirrer
  2. temperaturecooling tube
  3. customthermometer was purged by nitrogen gas
  4. dissolutionto dissolve at room temperature under nitrogen atmosphere
  5. temperaturesubsequently was heated at 70° C. for 1 hour
  6. stirringAfter stirring at 90° C. for 1 hour
  7. temperaturethe reaction mixture was cooled to room temperature
  8. stirringwith stirring
  9. filtrationThe resulting crystalline solid was filtered off
  10. washwashed with 5% by weight of acetic acid aqueous solution
  11. customdried at 80° C. for 20 hours under a reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-809c0d72a74341ac83c5e978963cd374
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084090B2

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