N-Methylformamide → 7-Bromo-3-methyl-3,4-dihydroquinazolin-4-one

HRID 1619293Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1619293
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([N+:11]([O-])=O)[CH:3]=1.[CH3:14][NH:15][CH:16]=O>O>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([C:6](=[O:7])[N:15]([CH3:16])[CH:14]=[N:11]2)=[CH:9][CH:10]=1

Komponenten

4

Edukt 2

HCID 31254N-MethylformamideHCID 37744674-Bromo-2-nitrobenzoic acid

Produkt 1

HCID 585745147-Bromo-3-methyl-3,4-dihydroquinazolin-4-oneAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 4-bromo-2-nitrobenzoic acid (1 g, 4.1 mmol) and InCl3 (0.88 g, 4 mmol) in N-methylformamide (6 mL, 100 mmol) was stirred at reflux overnight (ca. 18 h). After it was cooled to room temperature, the mixture was diluted with H2O (30 mL) and extracted with ethyl acetate (3×30 mL). The combined organic layers were washed with brine, and dried over Na2SO4. After filtration and concentration, the crude product was purified by column chromatography to give the desired product (0.5 g). MS (ESI): 239 (MH+).

Aufarbeitung

  1. temperatureat reflux overnight (ca. 18 h)
  2. extractionextracted with ethyl acetate (3×30 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration and concentration
  6. customthe crude product was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4995976578c748af8416eee18ba5dcff
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772301B2

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