Hydrochloric Acid → 8-Iodo-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 1958449

Reaktionsgleichung

Reaktionsgleichung von HRID 1958449
C([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[C:10]([I:17])[CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1)=[O:5])C.Cl>[OH-].[Na+].O>[I:17][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[NH:8][CH:7]=[C:6]([C:4]([OH:5])=[O:3])[C:15]2=[O:16]

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 12403679Ethyl 4-hydroxy-8-iodoquinoline-3-carboxylate

Produkt 1

HCID 218975788-Iodo-4-oxo-1,4-dihydroquinoline-3-carboxylic acidAusbeute 81,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

8-Iodo-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester (2 g, 5.83 mmol) was suspended in 10% NaOH in water (20 mL). The mixture was stirred under reflux for 1 h. The crude was cooled to room temperature and acidified with concentrated HCl. The solid was filtered off and thoroughly washed with water to afford 8-iodo-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid as a pinkish solid (1.5 g, 81.6%). 1H NMR (DMSO-d6, 400 MHz) δ 7.04 (t, 1H), 8.12-8.16 (m, 2H), 8.71 (s, 1H). Exact mass calculated for C10H6INO3 314.94, found 316 (MH+).

Aufarbeitung

  1. temperatureunder reflux for 1 h
  2. filtrationThe solid was filtered off
  3. washthoroughly washed with water

Quellen und Nachweise

ORD-Eintrag
ord-3211dd942d5c468db3bfedc864601eb4
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08410119B2

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