Sodium Carbonate → HCID 89462835, Verbindung

HRID 1525216Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1525216
[Br:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=O)=[CH:4][CH:3]=1.Cl.[OH:17][NH2:18].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[Br:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:18][OH:17])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 20145702(6-Bromopyridin-3-yl)(phenyl)methanone2×

Produkt 1

HCID 89462835HCID 89462835, VerbindungAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of (6-bromopyridin-3-yl)(phenyl)methanone, 4-b, (5.2 g, 20 mmol) in 100 ml of 95% ethanol was treated with N-hydroxylamine hydrochloride (4.2 g, 60 mmol) and sodium carbonate (6.36 g, 60 mmol). The resulting mixture was heated at reflux for 3 hours, cooled to room temperature, and concentrated under vacuum. The residue was taken into ethyl acetate (100 mL) followed by washing with water and brine (50 mL each). The organic layer was dried over sodium sulfate and concentrated. The resulting solid was recrystallized in ethyl acetate/petroleum ether to provide the product, 4-c, (2.7 g, 50%). 1H NMR (CD3OD, 300 MHz,): δ 8.34 (s, 1H), 7.78 (m, 1H), 7.32 (m, 7H).

Aufarbeitung

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 3 hours
  3. concentrationconcentrated under vacuum
  4. washby washing with water and brine (50 mL each)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe resulting solid was recrystallized in ethyl acetate/petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-9d12023385564e5c8f2ffb6e29538e80
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09079930B2

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