Phosphorus oxychloride → Benzyl-(2-chloro-3-nitro-pyridin-4-yl)-amine

HRID 639686Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 639686
[CH2:1]([NH:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11](O)[C:10]=1[N+:16]([O-:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:21])=O>C(#N)C.[Cl-].C([N+](CC)(CC)CC)C>[CH2:1]([NH:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([Cl:21])[C:10]=1[N+:16]([O-:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 178526800HCID 178526800, Verbindung

Produkt 1

HCID 72697848Benzyl-(2-chloro-3-nitro-pyridin-4-yl)-amineAusbeute 89,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 5946Tetraethylammonium ChlorideKatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

4-benzylamino-3-nitro-pyridin-2-ol (6.15 g, 25.07 mmol) was suspended in 100 mL of acetonitrile then phosphorus oxychloride (12 mL, 125.40 mmol) was added followed by tetraethyl ammonium chloride (4.15 g, 25.07 mmol) and the mixture was stirred at 85° C. overnight. The solvent was removed in vacuo and the residue was suspended in water (300 mL) and extracted with dichloromethane (2×200 mL). The organic layer was dried over magnesium sulfate and the solvent was removed in vacuo to give 5.9 g of the title compound as a yellow solid.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. extractionextracted with dichloromethane (2×200 mL)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customthe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7a553537354c49c4bd15ef6212e3b2da
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691877B2

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