Sodium Azide → 2-Azidomethyl-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one

HRID 1900715

Reaktionsgleichung

Reaktionsgleichung von HRID 1900715
CS(O[CH2:6][CH:7]1[O:21][C:10]2=[C:11]3[C:16](=[C:17]([CH3:19])[CH:18]=[C:9]2[CH2:8]1)[NH:15][C:14](=[O:20])[CH:13]=[CH:12]3)(=O)=O.[N-:22]=[N+:23]=[N-:24].[Na+]>CN(C)C=O>[N:22]([CH2:6][CH:7]1[O:21][C:10]2=[C:11]3[C:16](=[C:17]([CH3:19])[CH:18]=[C:9]2[CH2:8]1)[NH:15][C:14](=[O:20])[CH:13]=[CH:12]3)=[N+:23]=[N-:24]

Komponenten

4

Edukt 2

HCID 33557Sodium AzideHCID 233696442-Methanesulfonyloxymethyl-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one

Produkt 1

HCID 233697182-Azidomethyl-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mesyl compound (Example 3, 1 g) and sodium azide were added to dimethylformamide (20 ml), and the mixture was stirred at 100° C. for 50 minutes. After completion of the reaction, pressure was reduced to concentrate the mixture. The concentrate was diluted with a solvent mixture of chloroform and methanol (5:1), washed with water, and dried. When the solvent was evaporated, 759 mg of the title compound was obtained (91.6%). This substance was recrystallized from a solvent mixture of chloroform-n-hexane, obtaining yellow powdery crystals having a melting point of 192°-194° C.(dec.).

Aufarbeitung

  1. customAfter completion of the reaction, pressure
  2. concentrationto concentrate the mixture
  3. additionThe concentrate was diluted with a solvent mixture of chloroform and methanol (5:1)
  4. washwashed with water
  5. customdried
  6. customWhen the solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-c4e14bbe56174e60b6212cbcd8cd8df9
Quelldatensatz
uspto-grants-1996_11
Patentnummer
US05576324

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