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

HRID 1985628Notes

Reaction equation

HRID 1985628 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-de8eb69d4608436ba8501095be7fa580
Source dataset
uspto-grants-2009_06
Patent number
US07547679B2

Reaction notes

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