Methyl iodide → 3-[1-(3-Carboxy-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-quinolyl)-3-pyrrolidinyl]-1-methylpyridinium iodide

HRID 1588325Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1588325
[I:1][CH3:2].[CH:3]1([N:6]2[C:15]3[C:10](=[CH:11][C:12]([F:27])=[C:13]([N:16]4[CH2:20][CH2:19][CH:18]([C:21]5[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=5)[CH2:17]4)[CH:14]=3)[C:9](=[O:28])[C:8]([C:29]([OH:31])=[O:30])=[CH:7]2)[CH2:5][CH2:4]1>C(#N)C>[I-:1].[C:29]([C:8]1[C:9](=[O:28])[C:10]2[C:15](=[CH:14][C:13]([N:16]3[CH2:20][CH2:19][CH:18]([C:21]4[CH:22]=[N+:23]([CH3:2])[CH:24]=[CH:25][CH:26]=4)[CH2:17]3)=[C:12]([F:27])[CH:11]=2)[N:6]([CH:3]2[CH2:4][CH2:5]2)[CH:7]=1)([OH:31])=[O:30]

Komponenten

4

Edukt 2

HCID 6328Methyl iodideHCID 152303261-Cyclopropyl 6-fluoro-1,4-dihydro-4-oxo-7-[3-(3-pyridinyl)-1-pyrrolidinyl]-3-quinolinecarboxylic acid

Produkt 1

HCID 152303283-[1-(3-Carboxy-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-quinolyl)-3-pyrrolidinyl]-1-methylpyridinium iodideAusbeute 88,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Iodomethane (1.62 g, 11.4 mmol) was added dropwise to a stirred suspension of 1-cyclopropyl 6-fluoro-1,4-dihydro-4-oxo-7-[3-(3-pyridinyl)-1-pyrrolidinyl]-3-quinolinecarboxylic acid (0.30 g, 0.8 mmol) in acetonitrile (30 mL). The resulting mixture was heated at reflux for 2 hours. The suspension was then filtered, the solids were washed with acetonitrile and ether, and dried in vacuo at 40° C. to give the title compound (0.38 g, 88%) as a light yellow solid, mp 278°-280° C.

Aufarbeitung

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 2 hours
  3. filtrationThe suspension was then filtered
  4. washthe solids were washed with acetonitrile and ether
  5. customdried in vacuo at 40° C.

Quellen und Nachweise

ORD-Eintrag
ord-585db01955c546fca80a566100063486
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05221676

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