Formamide → 8-Nitroquinazolin-4-ol

HRID 513741

Reaktionsgleichung

Reaktionsgleichung von HRID 513741
[CH:1]([NH2:3])=O.[NH2:4][C:5]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][CH:11]=[CH:10][C:6]=1[C:7](O)=[O:8]>COC(O)C>[N+:14]([C:13]1[CH:12]=[CH:11][CH:10]=[C:6]2[C:5]=1[N:4]=[CH:1][NH:3][C:7]2=[O:8])([O-:16])=[O:15]

Komponenten

4

Edukt 2

HCID 713FormamideHCID 2196332-Amino-3-nitrobenzoic acid

Produkt 1

HCID 1354087998-Nitroquinazolin-4-olAusbeute 14,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 30156371-MethoxyethanolLösungsmittel

Versuchsvorschrift

Formamide (17.1 g, 380 mmol) was added to a solution of 2-amino-3-nitrobenzoic acid (2.0 g, 11 mmol) in methoxy ethanol (5 ml) and the reaction was heated at 200 C in a sealed tube for 17 h. After cooling, the mixture was concentrated in vacuo. The residue was quenched with sat. aq. NaHCO3 solution and the aqueous phase was extracted with EtOAc (100 ml, ×2). The combined organic phases were dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography with DCM as the eluent to give the title compound (300 mg, 14%).

Aufarbeitung

  1. temperaturethe reaction was heated at 200 C in a sealed tube for 17 h
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated in vacuo
  4. customThe residue was quenched with sat. aq. NaHCO3 solution
  5. extractionthe aqueous phase was extracted with EtOAc (100 ml, ×2)
  6. dry with materialThe combined organic phases were dried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified by column chromatography with DCM as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-67fde05214b644d69083949debd3385c
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102688B2

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