Reaktion #667779

Reaktionsgleichung

7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

cis-3-t-butoxycarbonylamino-4-methylpyrrolidine

DBU

→

title compound

Ausbeute 8.9%

7-(cis-3-Amino-4-methyl-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Ausbeute 8.9%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed for 52 hours
2. 2
   TemperaturAfter cooling
3. 3
   Filtrationthe resulting precipitate was collected by filtration
4. 4
   Waschenwashed with chilled acetonitrile
5. 5
   workup.ADDITIONthis was added to concentrated hydrochloric acid-methanol (1:1, 5 ml)
6. 6
   FiltrationThe reacting mixture was collected by filtration
7. 7
   Waschenwashed with chilled water sufficiently
8. 8
   Sonstigerecrystallized from chloroform-methanol-concentrated aqueous ammonia (10:10:3)

Vorschrift

A mixture of 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (0.7 g), cis-3-t-butoxycarbonylamino-4-methylpyrrolidine (0.62 g), DBU (0.43 g) and anhydrous acetonitrile (30 ml) was refluxed for 52 hours. After cooling, the resulting precipitate was collected by filtration, washed with chilled acetonitrile and this was added to concentrated hydrochloric acid-methanol (1:1, 5 ml) and stirred for 40 minutes at elevated temperature. The reacting mixture was collected by filtration, washed with chilled water sufficiently and recrystallized from chloroform-methanol-concentrated aqueous ammonia (10:10:3) to give the title compound (0.076 g) as pale yellow prisms, mp 268°-270° C. (decompd.).

Quelle