Chloroform → (+)-2-Formylaminomethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one

HRID 1900758Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1900758
[NH2:1][CH2:2][CH:3]1[O:17][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH2:4]1)[NH:11][C:10](=[O:16])[CH:9]=[CH:8]3.C(Cl)(Cl)Cl.[C:22](OC(=O)C)(=[O:24])C.C(OC=O)=O>O1CCCC1.CCOCC>[CH:22]([NH:1][CH2:2][CH:3]1[O:17][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH2:4]1)[NH:11][C:10](=[O:16])[CH:9]=[CH:8]3)=[O:24]

Komponenten

7

Edukt 4

HCID 6212ChloroformHCID 7918Acetic AnhydrideHCID 9548680Formic anhydrideHCID 233695672-Aminomethyl-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one

Produkt 1

HCID 23369729(+)-2-Formylaminomethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

(+)-2-Aminomethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one (1.17 g, 5.08 mmol) was suspended in tetrahydrofuran (30 ml)--chloroform (30 ml). To the suspension, acetic anhydride--formic anhydride (2.24 g, 25.4 mmol) was added, and refluxed with heat in a bath of 70° C. for 3 hours. The resulting reaction mixture was cooled at room temperature, and combined with ether. The insoluble matter, which was collected by filtration, was recrystallized from chloroform--methanol--ether. As a result, 460 mg of the title compound was obtained as colorless powder (35.1%).

Aufarbeitung

  1. temperaturerefluxed
  2. customThe resulting reaction mixture
  3. temperaturewas cooled at room temperature
  4. filtrationThe insoluble matter, which was collected by filtration
  5. customwas recrystallized from chloroform

Quellen und Nachweise

ORD-Eintrag
ord-ee8cc227b1ce4f5fb8424173ad72672b
Quelldatensatz
uspto-grants-1996_11
Patentnummer
US05576324

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