Benzophenone imine → 6-(Benzhydrylidene-amino)-1-ethyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester

HRID 1985628Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1985628
CC(C)([O-])C.[Na+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.[CH2:53]([O:55][C:56]([C:58]1[C:67](=[O:68])[C:66]2[C:61](=[CH:62][CH:63]=[C:64](I)[CH:65]=2)[N:60]([CH2:70][CH3:71])[CH:59]=1)=[O:57])[CH3:54].[C:72](=[NH:85])([C:79]1[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=1)[C:73]1[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[CH2:53]([O:55][C:56]([C:58]1[C:67](=[O:68])[C:66]2[C:61](=[CH:62][CH:63]=[C:64]([N:85]=[C:72]([C:73]3[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=3)[C:79]3[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=3)[CH:65]=2)[N:60]([CH2:70][CH3:71])[CH:59]=1)=[O:57])[CH3:54]

Komponenten

7

Edukt 4

HCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 57720090Ethyl 1-ethyl-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate

Produkt 1

HCID 577200706-(Benzhydrylidene-amino)-1-ethyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl esterAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A Pyrex tube was charged with sodium tert-butoxide (1.4 mmol), Pd2(dba)3 (0.00125 mmol), and BINAP (0.00375 mmol). The Pyrex tube was fitted with a septum and after the air atmosphere was replaced with argon, toluene (4 mL), 1-ethyl-6-iodo-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester (1.0 mmol), and benzophenone imine (1.2 mmol) were added by syringe. The reaction was sealed and heated to 80° C. with stirring until starting material was consumed as judged by GC analysis. The reaction mixture was cooled to room temperature, diluted with ether (40 mL), filtered, and concentrated. The crude reaction mixture was then recrystallized from MeOH to furnish the desired product in 90% yield.

Aufarbeitung

  1. customThe Pyrex tube was fitted with a septum
  2. additionwere added by syringe
  3. customThe reaction was sealed
  4. customwas consumed
  5. temperatureThe reaction mixture was cooled to room temperature
  6. additiondiluted with ether (40 mL)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude reaction mixture
  10. customwas then recrystallized from MeOH

Quellen und Nachweise

ORD-Eintrag
ord-de8eb69d4608436ba8501095be7fa580
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07547679B2

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