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

HRID 1985628ノート

反応式

HRID 1985628 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-de8eb69d4608436ba8501095be7fa580
出典データセット
uspto-grants-2009_06
特許番号
US07547679B2

反応ノート

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