Reaktion #1391

ord-4dd793d179ff43a5b9d3cc139df171bf

Reaktionsgleichung

Cc1c(F)c(Br)cc2c1c(=O)c(C(=O)O)cn2C1CC1
1-cyclopropyl-6-fluoro-7-bromo-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
O=C1CCNCC1
4-oxopiperidine
Cc1c(F)c(N2CCC(=O)CC2)cc2c1c(=O)c(C(=O)O)cn2C1CC1
1-cyclopropyl-6-fluoro-7-(4-oxo-1-piperidinyl)-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
Ausbeute 37.6%

Reaktionsbedingungen

Temperatur
90°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.DISTILLATIONThe solvent is distilled off under reduced pressure
  2. 2
    workup.ADDITIONTo the resulting residue is added ethanol
  3. 3
    Filtrationthe precipitated crystals are filtered

Vorschrift

To a solution of 1-cyclopropyl-6-fluoro-7-bromo-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.58 g) in N-methyl-2-pyrrolidone (5 ml) is added 4-oxopiperidine (0.64 g) and the mixture is heated at 90° C. for 20 minutes. The solvent is distilled off under reduced pressure. To the resulting residue is added ethanol and the precipitated crystals are filtered to give 1-cyclopropyl-6-fluoro-7-(4-oxo-1-piperidinyl)-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (230 mg).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05723648uspto-grants-1998_03