Pyridine → 5-Methoxyisophthalonitrile

HRID 431847Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 431847
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]([NH2:14])=O)[CH:6]=[C:7]([CH:11]=1)[C:8]([NH2:10])=O.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]#[N:14])[CH:6]=[C:7]([CH:11]=1)[C:8]#[N:10]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 21942402HCID 21942402, Verbindung

Produkt 1

HCID 219424235-MethoxyisophthalonitrileAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A suspension of the 5-methoxyisophthalamide (3.1 g, 16 mmol) in a dichloromethane (27 mL) at 0° C. was treated with pyridine (5.2 mL, 65 mol) and then trifluoroacetic anhydride drop-wise (5.4 mL, 39 mmol). The reaction was stirred at 0° C. for 20 minutes and then stirred overnight at ambient temperature. The reaction mixture was washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated. Silica gel chromatography using hexanes:ethyl acetate:dichloromethane afforded 940 mg (46%) of the 5-methoxyisophthalonitrile as a white solid.

Aufarbeitung

  1. stirringstirred overnight at ambient temperature
  2. washThe reaction mixture was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0d45eb141f164b05873630dcc9427728
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06660753B2

Notizen zur Reaktion

Wird geladen…