Acetic Acid → 7-Methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile

HRID 2213785

Reaktionsgleichung

Reaktionsgleichung von HRID 2213785
C([Li])CCC.[C:6](#[N:8])[CH3:7].CN(/[CH:12]=[N:13]/[C:14]1[C:15]([C:26]([O:28]C)=O)=[CH:16][C:17]2[C:22]([CH:23]=1)=[CH:21][CH:20]=[C:19]([O:24][CH3:25])[CH:18]=2)C.C(O)(=O)C>O1CCCC1>[CH3:25][O:24][C:19]1[CH:20]=[CH:21][C:22]2[CH:23]=[C:14]3[C:15]([C:26](=[O:28])[C:7]([C:6]#[N:8])=[CH:12][NH:13]3)=[CH:16][C:17]=2[CH:18]=1

Komponenten

6

Edukt 4

HCID 176Acetic Acid2×HCID 6342AcetonitrileHCID 178418339ButyllithiumHCID 178496951HCID 178496951, Verbindung

Produkt 1

HCID 98136637-Methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 4.75 mL (11.88 mmol) of n-butyllithium (2.5M in hexane) in 4.0 mL of tetrahydrofuran at −78° C. is added dropwise a solution of 0.68 mL (13.1 mmol) of acetonitrile in 6.8 mL of tetrahydrofuran. After completion of addition, the suspension is stirred for 10 minutes. To this is added 1.36 g (4.75 mmol) of methyl 3-{[(E)-(dimethylamino)methylidene]amino}-7-methoxy-2-naphthoate in 32 mL of tetrahydrofuran dropwise. The resulting reaction mixture is stirred at −78° C. for 1 hour, at −5° C. for 1 hour and at room temperature for 15 minutes. The reaction mixture is again cooled to −78° C. and 1.72 g (28.6 mmol) of acetic acid is added dropwise. After addition of the acetic acid, the reaction mixture is allowed to warm to room temperature. The precipitate is collected by filtration and washed sequentially with water, acetonitrile and methanol. After drying in vacuo, this yields 796.9 mg (67%) of 7-methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile as a deep yellow solid, mp>260° C.

Aufarbeitung

  1. additionAfter completion of addition
  2. customThe resulting reaction mixture
  3. stirringis stirred at −78° C. for 1 hour, at −5° C. for 1 hour and at room temperature for 15 minutes
  4. temperatureto warm to room temperature
  5. filtrationThe precipitate is collected by filtration
  6. washwashed sequentially with water, acetonitrile and methanol
  7. customAfter drying in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-44e212385697476eaac688ef198c6546
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07105531B2

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