Urea → 1,3(2H,4H)-isoquinolinedione

HRID 432670Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 432670
[C:1]([OH:13])(=O)[CH2:2][C:3]1[C:4](=[CH:8][CH:9]=[CH:10][CH:11]=1)[C:5](O)=[O:6].[NH2:14]C(N)=O>CO>[C:1]1(=[O:13])[NH:14][C:5](=[O:6])[C:4]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:3]2[CH2:2]1

Komponenten

4

Edukt 2

HCID 1176UreaHCID 66643Homophthalic acid

Produkt 1

HCID 3494351,3(2H,4H)-isoquinolinedioneAusbeute 34,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

A mixture of homophthalic acid (200 g, 1.09 mol) and urea (80 g, 1.31 mol) was ground to a fine powder then heated at 175-185° C. until it had melted then resolidified. The mixture was cooled to ambient temperature, methanol (500 ml) was added, then the mixture was heated under reflux for 20 minutes, filtered, and allowed to cool to ambient temperature. The resulting solid was collected by filtration, washed with methanol and dried in vacuo to give homophthalimide (60 g, 34%) as a solid; m.pt. 235-240° C.; δH 4.0 (2H, s), 7.3-7.75 (3H, m), 8.10 (1H, d), 11.20 (1H, br s).

Aufarbeitung

  1. temperatureThe mixture was cooled to ambient temperature
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 20 minutes
  4. filtrationfiltered
  5. temperatureto cool to ambient temperature
  6. filtrationThe resulting solid was collected by filtration
  7. washwashed with methanol
  8. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-08508139bc56446fa9125aeb8ce2c57e
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06664269B2

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