Acetic Acid → 3-Quinolinecarbonitrile, 7-ethoxy-1,4-dihydro-6-methoxy-4-oxo-

HRID 1935031Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1935031
C([Li])CCC.[C:6](#[N:8])[CH3:7].[CH2:9]([O:11][C:12]1[C:21]([O:22][CH3:23])=[CH:20][C:15]([C:16]([O:18]C)=O)=[C:14]([N:24]=[CH:25]N(C)C)[CH:13]=1)[CH3:10].C(O)(=O)C>C1COCC1.O>[CH2:9]([O:11][C:12]1[CH:13]=[C:14]2[C:15]([C:16](=[O:18])[C:7]([C:6]#[N:8])=[CH:25][NH:24]2)=[CH:20][C:21]=1[O:22][CH3:23])[CH3:10]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 6342AcetonitrileHCID 10779127Methyl 4-ethoxy-5-methoxy-2-(dimethylaminomethyleneamino)benzoateHCID 178418339Butyllithium

Produkt 1

HCID 104904723-Quinolinecarbonitrile, 7-ethoxy-1,4-dihydro-6-methoxy-4-oxo-Ausbeute 83,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Added 54.0 ml (135 mmol) n-butyl lithium to 150 ml THF and chilled to −78° C. under N2. Added dropwise over 20 minutes 7.05 ml (135 mmol) acetonitrile in 200 ml THF. Stirred 15 minutes and added a solution of 17.99 g (64.2 mmol) methyl 4-ethoxy-5-methoxy-2-(dimethylaminomethyleneamino)benzoate in 150 ml THF dropwise over 20 minutes. Let stir for 0.5 hour at −78° C. Added 11.0 ml (193 mmol) acetic acid and warmed gradually to 25° C. After 2.5 hours, stripped solvent, slurried residue with water, collected solids and dried in vacuo, giving 13.025 g of yellow solid: mass spectrum (electrospray m/e): M+H=245.2.

Aufarbeitung

  1. stirringLet stir for 0.5 hour at −78° C
  2. temperaturewarmed gradually to 25° C
  3. waitAfter 2.5 hours
  4. customcollected solids
  5. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-14721d2109de442eb5fcda7b0635176a
Quelldatensatz
uspto-grants-2002_05
Patentnummer
US06384051B1

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