3-Methylpyridine → 7-(3-Aminomethyl-4-methyl-1-pyrrolidinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 580571

Reaktionsgleichung

Reaktionsgleichung von HRID 580571
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[CH:8][N:9]2[CH2:12][CH3:13])=[CH:4][C:3]=1[F:18].N1C=CC=C(C)C=1.[NH2:26][CH2:27][CH:28]1[CH:32]([CH3:33])[CH2:31][NH:30][CH2:29]1>N>[NH2:26][CH2:27][CH:28]1[CH:32]([CH3:33])[CH2:31][N:30]([C:2]2[CH:11]=[C:10]3[C:5]([C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[CH:8][N:9]3[CH2:12][CH3:13])=[CH:4][C:3]=2[F:18])[CH2:29]1

Komponenten

5

Edukt 3

HCID 79703-MethylpyridineHCID 4831697-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 4583498(4-Methylpyrrolidin-3-yl)methanamine

Produkt 1

HCID 139330927-(3-Aminomethyl-4-methyl-1-pyrrolidinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidAusbeute 21,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 222AmmoniaLösungsmittel

Versuchsvorschrift

A mixture of 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (0.5 g), β-picoline (11 ml) and 3-aminomethyl-4-methylpyrrolidine (0.5 g) was refluxed for 8.5 hours, then the reacting mixture was cooled to room temperature. To the mixture was added concentrated aqueous ammonia (100 ml) and concentrated under reduced pressure. To the residue was added dichloromethane-ether (1:3, 37 ml), the resulting precipitate was collected by filtration, washed with ethanol-ether (1:3), recrystallized from ethanol and further recrystallized from chloroform-methanol-concentrated aqueous ammonia (10:10:1) to give the title compound (0.14 g) as pale yellow powder, mp 245°-248° C.

Aufarbeitung

  1. temperaturewas refluxed for 8.5 hours
  2. concentrationconcentrated under reduced pressure
  3. additionTo the residue was added dichloromethane-ether (1:3, 37 ml)
  4. filtrationthe resulting precipitate was collected by filtration
  5. washwashed with ethanol-ether (1:3)
  6. customrecrystallized from ethanol
  7. customfurther recrystallized from chloroform-methanol-concentrated aqueous ammonia (10:10:1)

Quellen und Nachweise

ORD-Eintrag
ord-f139f10be90c4dafa9e9508b53e7e7e3
Quelldatensatz
uspto-grants-1988_06
Patentnummer
US04753953

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