3-Pyrrolidinemethanamine → 7-[3-(Aminomethyl)-1-pyrrolidinyl]-1-ethyl-5,6,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 542473Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 542473
[CH2:1]([N:3]1[C:12]2[C:7](=[C:8]([F:16])[C:9]([F:15])=[C:10](F)[C:11]=2[F:13])[C:6](=[O:17])[C:5]([C:18]([OH:20])=[O:19])=[CH:4]1)[CH3:2].[NH:21]1[CH2:25][CH2:24][CH:23]([CH2:26][NH2:27])[CH2:22]1>C(#N)C.C(OCC)C>[NH2:27][CH2:26][CH:23]1[CH2:24][CH2:25][N:21]([C:10]2[C:11]([F:13])=[C:12]3[C:7]([C:6](=[O:17])[C:5]([C:18]([OH:20])=[O:19])=[CH:4][N:3]3[CH2:1][CH3:2])=[C:8]([F:16])[C:9]=2[F:15])[CH2:22]1

Komponenten

5

Edukt 2

HCID 50687753-PyrrolidinemethanamineHCID 138510191-Ethyl-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Produkt 1

HCID 138510207-[3-(Aminomethyl)-1-pyrrolidinyl]-1-ethyl-5,6,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

To 1.0 g (3.5 mmol) of 1-ethyl-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid in 20 ml of acetonitrile was added 1.05 g (6.9 mmol) of 1,8-diazobicyclo[5.4.0]undec-7-ene and 0.35 g (3.5 mmol) of 3-pyrrolidinemethanamine and the mixture was stirred at 45° C. for 18 hours, then refluxed one hour. The mixture was cooled, diluted with 50 ml of diethyl ether, and filtered. The solids were washed with ethanol and then diethyl ether to give 1.04 g (82%) of the title compound, mp>170° C. (decomposition).

Aufarbeitung

  1. temperaturerefluxed one hour
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. washThe solids were washed with ethanol

Quellen und Nachweise

ORD-Eintrag
ord-161784c58b764fa5b8e92a568880dff1
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04657913

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