Acetic Anhydride → furo(3,4-b)pyridin-5(7H)-one

HRID 280060

Reaktionsgleichung

Reaktionsgleichung von HRID 280060
[N:1]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:2]=1[C:3]([O:5][C:6]2=[O:11])=O.C(N1C2C(=CC=CC=2)C=C1C)CCCCCCC.C(N(CC)C1C=C(OCC)C=CC=1)C.C(OC(=O)C)(=O)C>C(O)(=O)C.[Cl-].[Zn+2].[Cl-]>[C:6]1([C:7]2[C:2](=[N:1][CH:10]=[CH:9][CH:8]=2)[CH2:3][O:5]1)=[O:11]

Komponenten

7

Edukt 4

HCID 7918Acetic AnhydrideHCID 69688Furo[3,4-b]pyridine-5,7-dioneHCID 74625N,N-Diethyl-m-phenetidineHCID 1707081H-Indole, 2-methyl-1-octyl-

Produkt 1

HCID 819439furo(3,4-b)pyridin-5(7H)-oneAusbeute 303,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

6.0 g of quinolinic anhydride, 9.5 g of N-octyl-2-methylindole and 0.56 g of zinc chloride are stirred in 30 ml of glacial acetic acid at 20° C. for 5 hours. 6.6 g of 3-diethylaminophenetole and 8 ml of acetic anhydride are then added, after which the mixture is stirred at 50° C. for 21/2 hours. The product is precipitated with 30% aqueous ammonia, separated from the aqueous phase and recrystallised from isopropanol, affording 16.5 g of the isomer-free 4-azaphthalide compound of the formula ##STR16## of melting point 113°-118° C.

Aufarbeitung

  1. customThe product is precipitated with 30% aqueous ammonia
  2. customseparated from the aqueous phase
  3. customrecrystallised from isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-3aea14e105664764a1ddfa9feaffda81
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04587539

Verknüpfte Notizen

Wird geladen…