Hydrochloric Acid → 10-Fluoroindolo[2,1-b]quinazoline-6,12-dione

HRID 215795

Reaktionsgleichung

Reaktionsgleichung von HRID 215795
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8](=O)[C:7]2=[O:12].[C:13]12[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=1)[NH:18]C(=O)O[C:14]2=[O:15].CN(C1C=CC=CN=1)C.Cl>N1C=CC=CC=1.C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]1[C:8](=[N:18][C:19]3[C:13]([C:14]1=[O:15])=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:7]2=[O:12]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 8359Isatoic AnhydrideHCID 218852-DimethylaminopyridineHCID 5864187-Fluoroisatin

Produkt 1

HCID 47865210-Fluoroindolo[2,1-b]quinazoline-6,12-dioneAusbeute 14 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A solution of 7-fluoroisatin (300 mg, 1.8 mmol), isatoic anhydride (1.2 g, 7.3 mmol), and dimethylaminopyridine (222 mg, 2 mmol) in 5 mL of pyridine were heated at reflux temperature for 64 h. 50 mL of 0.2N HCl and 100 mL of chloroform were added and the chloroform layer was separated. The water layer was extracted with chloroform and the combined organic extracts were concentrated. Chromatography on silica gel eluting with chloroform gave the title compound in 14% yield: mp 264-267° C.; 1H NMR (300 MHz, CDCl3) δ 8.46 (d, 1H) 8.02 (d, 1H) 7.82-7.92 (m, 1H) 7.79 (d, 1H) 7.64-7.74 (m, 1H) 7.52-7.64 (m, 1H) 7.40-7.49 (m, 1H).

Aufarbeitung

  1. temperatureat reflux temperature for 64 h
  2. customthe chloroform layer was separated
  3. extractionThe water layer was extracted with chloroform
  4. concentrationthe combined organic extracts were concentrated

Quellen und Nachweise

ORD-Eintrag
ord-7b161f3376b04438970a1c230d185360
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193185B2

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