Lithium Chloride → 4-Chloro-5-[4-methoxy-3-(2-methoxyethoxy)phenyl]nicotinonitrile

HRID 506157

Reaktionsgleichung

Reaktionsgleichung von HRID 506157
COC1C=C(C=CC=1OC)C[N:7]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH2:22][CH2:23][O:24][CH3:25])[CH:14]=2)[C:10](=O)[C:9]([C:27]#[N:28])=[CH:8]1.[Cl-:34].[Li+]>O=P(Cl)(Cl)Cl>[Cl:34][C:10]1[C:9]([C:27]#[N:28])=[CH:8][N:7]=[CH:12][C:11]=1[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH2:22][CH2:23][O:24][CH3:25])[CH:14]=1

Komponenten

4

Edukt 2

HCID 433294Lithium ChlorideHCID 68466370HCID 68466370, Verbindung

Produkt 1

HCID 684653034-Chloro-5-[4-methoxy-3-(2-methoxyethoxy)phenyl]nicotinonitrileAusbeute 78,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24813Phosphorus oxychlorideLösungsmittel

Versuchsvorschrift

A solution of 1-(3,4-dimethoxybenzyl)-5-[4-methoxy-3-(2-methoxyethoxy)phenyl]-4-oxo-1,4-dihydro-pyridine-3-carbonitrile (300 mg, 0.666 mmol) and lithium chloride (LiCl, 254 mg, 6 mmol) in 2.5 mL of POCl3 was heated at reflux for 2.5 h. The excess POCl3 was removed by evaporating in vacuo and then was co-evaporated with toluene. The residue was dissolved in 100 mL ethyl acetate and washed with ice-cold 1 N aqueous sodium hydroxide. The organic layer was separated, dried over anhydrous MgSO4, filtered, and concentrated in vacuo, and the resulting solid was triturated with isopropyl alcohol to yield 166 mg (78% yield) of 4-chloro-5-[4-methoxy-3-(2-methoxyethoxy)phenyl]-nicotinonitrile as an off-white solid.

Aufarbeitung

  1. temperatureat reflux for 2.5 h
  2. customThe excess POCl3 was removed
  3. customby evaporating in vacuo
  4. dissolutionThe residue was dissolved in 100 mL ethyl acetate
  5. washwashed with ice-cold 1 N aqueous sodium hydroxide
  6. customThe organic layer was separated
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customthe resulting solid was triturated with isopropyl alcohol

Quellen und Nachweise

ORD-Eintrag
ord-ab54470b12b343b68d52b0f62a9f8211
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781591B2

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