Reaktion #76168

ord-8632f70cb72443d0a76c0ea95c5c2000

Reaktionsgleichung

COC(=O)c1cn(C2CC2)c2c(OC)c(Cl)c(F)cc2c1=O
methyl 1-cyclopropyl-7-chloro-6-fluoro-8-methoxy-1,4-dihydro-4-oxo-3-quinolinecarboxylate
CC(=O)[O-]
acetate
O=S(=O)(O)O
sulfuric acid
COc1c(Cl)c(F)cc2c(=O)c(C(=O)O)cn(C3CC3)c12
1-cyclopropyl-7-chloro-6-fluoro-8-methoxy-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid
Ausbeute 92.0%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    TemperaturThe resulting mixture was cooled
  2. 2
    Filtrationfiltered
  3. 3
    SonstigeThe precipitate was re-crystallized from choroform-ethanol

Vorschrift

28.6 g of methyl 1-cyclopropyl-7-chloro-6-fluoro-8-methoxy-1,4-dihydro-4-oxo-3-quinolinecarboxylate (0.088 mol), 160 ml of acetate acid, 100 ml of water and 18 ml of concentrated sulfuric acid were stirred for 40 minutes at 100-110° C. The resulting mixture was cooled and filtered. The precipitate was re-crystallized from choroform-ethanol to afford 25.2 g of 1-cyclopropyl-7-chloro-6-fluoro-8-methoxy-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (Gaticarboxylic acid, 0.081 mol) in 91.8% yield, mp 195-199° C.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06699992B2uspto-grants-2004_03