Reaktion #501068

ord-98c9fe8dd6d04dc7a70045c79dfddcc6

Reaktionsgleichung

Nc1cccc(Cl)c1
m-Chloroaniline
CCOC(=O)C(CC(C)=O)C(=O)c1ccccc1
2-benzoyl-4-oxo-pentanoic acid ethyl ester
Cc1ccc(S(=O)(=O)O)cc1
tosic acid
→
CCOC(=O)c1cc(C)n(-c2cccc(Cl)c2)c1-c1ccccc1
product
CCOC(=O)c1cc(C)n(-c2cccc(Cl)c2)c1-c1ccccc1
1-(3-Chlorophenyl)-5-methyl-2-phenyl-1H-pyrrole-3-carboxylic Acid Ethyl Ester

Edukte

Nc1cccc(Cl)c1
m-Chloroaniline
CCOC(=O)C(CC(C)=O)C(=O)c1ccccc1
2-benzoyl-4-oxo-pentanoic acid ethyl ester
Cc1ccc(S(=O)(=O)O)cc1
tosic acid

Reagenzien

Keine

Lösungsmittel

CCO
ethanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturheated
  2. 2
    Temperaturunder reflux
  3. 3
    SonstigeUpon completion of the reaction
  4. 4
    Sonstigethe crude solid was recrystallized from ethanol

Vorschrift

m-Chloroaniline (5 mmol, 0.6 g), 2-benzoyl-4-oxo-pentanoic acid ethyl ester (5 mmol, 1.2 g), and tosic acid (0.1 g) were combined in ethanol, then heated under reflux. Upon completion of the reaction, the crude solid was recrystallized from ethanol to provide the named product (m.p. 93.2° C.-94.6° C.).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06569890B2uspto-grants-2003_05