Hydrochloric Acid → 1,4-Dihydro-2-(methylthio)-4-oxo-3-quinolinecarboxylic acid

HRID 401229Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 401229
C([O:3][C:4]([C:6]1[C:7]([S:17][CH3:18])=[N:8][C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:5])C.Cl>[OH-].[Na+]>[CH3:18][S:17][C:7]1[NH:8][C:9]2[C:14]([C:15](=[O:16])[C:6]=1[C:4]([OH:5])=[O:3])=[CH:13][CH:12]=[CH:11][CH:10]=2

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 1784701074-Hydroxy-2-methylsulfanyl-quinoline-3-carboxylic acid ethyl ester

Produkt 1

HCID 465076311,4-Dihydro-2-(methylthio)-4-oxo-3-quinolinecarboxylic acidAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

4-Hydroxy-2-methylsulfanyl-quinoline-3-carboxylic acid ethyl ester (8 g, 30 mmol) was heated under reflux in NaOH solution (10%, 100 mL) for 1.5 h. After cooling, the mixture was acidified with concentrated HCl to pH 4. The resulting solid was collected via filtration, washed with water (100 mL) and MeOH (100 mL) to give 2-methylsulfanyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (A-16) as a white solid (6 g, 85%). 1H NMR (CDCl3) δ 16.4 (br s, 1H), 11.1 (br s, 1H), 8.19 (d, J=8 Hz, 1H), 8.05 (d, J=8 Hz, 1H), 7.84 (t, J=8, 8 Hz, 1H), 7.52 (t, J=8 Hz, 1H), 2.74 (s, 3H); ESI-MS 235.9 m/z (MH+).

Aufarbeitung

  1. temperatureAfter cooling
  2. filtrationThe resulting solid was collected via filtration
  3. washwashed with water (100 mL) and MeOH (100 mL)

Quellen und Nachweise

ORD-Eintrag
ord-555753fc7dba438cb2bfee8522159992
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741925B2

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