Hydrochloric Acid → 7-Methoxy-2-oxo-8-pentyloxy-1,2-dihydroquinoline-3-carboxylic acid

HRID 393264Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 393264
C[O:2][C:3]([C:5]1[C:6](=[O:23])[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([O:15][CH3:16])[C:9]=2[O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:4].[OH-].[Na+].Cl>CO.O>[CH3:16][O:15][C:10]1[C:9]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[C:8]2[C:13]([CH:14]=[C:5]([C:3]([OH:4])=[O:2])[C:6](=[O:23])[NH:7]2)=[CH:12][CH:11]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 98618427-Methoxy-2-oxo-8-pentyloxy-1,2-dihydroquinoline-3-carboxylic acid methyl ester

Produkt 1

HCID 99045957-Methoxy-2-oxo-8-pentyloxy-1,2-dihydroquinoline-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

7-Methoxy-2-oxo-8-pentyloxy-1,2-dihydroquinoline-3-carboxylic acid methyl ester (240 mg) obtained in Example 1-1 was dissolved in methanol (7 ml) and water (3 ml), to which sodium hydroxide (120 ml) was added, and the solution was stirred at room temperature for 1.5 hours. While the reaction vessel was cooled with ice, the solution was acidified with the addition of concentrated hydrochloric acid, and extracted with ethyl acetate (20 ml). The organic layer was dried over anhydrous sodium sulfate, filtered to remove the desiccating agent, and concentrated under reduced pressure to give the title compound (228 ml) (Table 6).

Aufarbeitung

  1. temperatureWhile the reaction vessel was cooled with ice
  2. extractionextracted with ethyl acetate (20 ml)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customto remove the desiccating agent
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8e46500f16ff4f08bd68b27a80237437
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06806276B2

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