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

HRID 1985628노트

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HRID 1985628 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-de8eb69d4608436ba8501095be7fa580
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07547679B2

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