Triethylamine → 1-Ethyl-6-chloro-7-(4-phthalidyl-1-piperazinyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 544227Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 544227
Cl.[CH2:2]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([Cl:20])=[C:11]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[CH:12]=2)[C:7](=[O:21])[C:6]([C:22]([OH:24])=[O:23])=[CH:5]1)[CH3:3].[OH:25][CH:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:28](=O)[O:27]1.C(N(CC)CC)C>CN(C=O)C>[CH2:2]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([Cl:20])=[C:11]([N:14]3[CH2:19][CH2:18][N:17]([CH:28]4[C:30]5[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=5)[C:26](=[O:25])[O:27]4)[CH2:16][CH2:15]3)[CH:12]=2)[C:7](=[O:21])[C:6]([C:22]([OH:24])=[O:23])=[CH:5]1)[CH3:3]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 38042593-Hydroxyisobenzofuran-1(3H)-oneHCID 12733912Defluoro-6-chloro Norfloxacin Hydrochloride

Produkt 1

HCID 133204541-Ethyl-6-chloro-7-(4-phthalidyl-1-piperazinyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acidAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 1-ethyl-6-chloro-7-(1-piperazinyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid hydrochloride 1.9 g (0.005 mole), 3-hydroxyphthalide 0.75 g (0.005 mole), triethylamine 0.5 g (0.005 mole) and DMF 10 ml was heated at 100°-110° C. for 8 hours under stirring. After cooling, the reaction mixture was evaporated under vacuum. The residue was dissolved in dichloromethane, washed with water and dried with anhydrous Na2SO4. After removing the solvent, the residue was recrystallized from a mixed solvent of DMF and ethanol to obtain 1.8 g (78%) of 1-ethyl-6-chloro-7-(4-phthalidyl-1-piperazinyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid. Colorless powders.

Aufarbeitung

  1. temperaturewas heated at 100°-110° C. for 8 hours
  2. temperatureAfter cooling
  3. customthe reaction mixture was evaporated under vacuum
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washwashed with water
  6. dry with materialdried with anhydrous Na2SO4
  7. customAfter removing the solvent
  8. customthe residue was recrystallized from a mixed solvent of DMF and ethanol

Quellen und Nachweise

ORD-Eintrag
ord-d450b48e86b8497f8a72b0c7f3d12299
Quelldatensatz
uspto-grants-1984_05
Patentnummer
US04448962

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