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

HRID 280058

Reaktionsgleichung

Reaktionsgleichung von HRID 280058
[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.N1C2C(=CC=CC=2)C=C1.[Cl-].[Ca+2].[Cl-].[Cl-].[Al+3].[Cl-].[Cl-].C(OC(=O)C)(=O)C.N>C(O)(=O)C.C(#N)C.[Cl-].[Zn+2].[Cl-].[Fe](Cl)Cl.[Co](Cl)Cl.[Cu](Cl)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

13

Edukt 6

HCID 222AmmoniaHCID 798IndoleHCID 7918Acetic AnhydrideHCID 69688Furo[3,4-b]pyridine-5,7-dioneHCID 5284359Calcium ChlorideHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 819439furo(3,4-b)pyridin-5(7H)-one

Reagenzien, Katalysatoren, Lösungsmittel 6

HCID 24014Cupric ChlorideKatalysatorHCID 24288Cobalt(II) chlorideKatalysatorHCID 24458Ferrous ChlorideKatalysatorHCID 3007855ZincchlorideKatalysatorHCID 176Acetic AcidLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A particularly advantageous embodiment of the novel process comprises dissolving or suspending quinolinic anhydride in a saturated aliphatic C2 -C4 -monocarboxylic acid, in particular acetic acid, or also in acetonitrile, adding an indole compound of the formula (7a) and stirring the mixture at room temperature in the presence of an inorganic metal salt, in particular a metal halide, of a polyvalent metal or atomic weight 26 to 66, for example zinc chloride, calcium chloride, aluminium chloride, iron chloride, cobalt chloride or copper dichloride, preferably for 2 to 6 hours. The compound of the formula (5a) is then added and, after addition of acetic anhydride, the reaction mixture is heated at 30° to 60° C., preferably for 1 to 3 hours. The pH is then adjusted to 7.5 to 9 for example with an alkali metal hydroxide or aqueous ammonia. The precipitated 4-azaphthalide compound of the formula (1a) is isolated and, if necessary, recrystallised.

Aufarbeitung

  1. dissolutionA particularly advantageous embodiment of the novel process comprises dissolving
  2. temperaturethe reaction mixture is heated at 30° to 60° C., preferably for 1 to 3 hours

Quellen und Nachweise

ORD-Eintrag
ord-d0e8178ae6be475bb5721a445bedd9ae
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04587539

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