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Water → 7-Hydroxy-4-hydroxyimino-6-methoxy-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester

HRID 279372
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 279372
[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([O:17][CH3:18])=[C:13]([OH:16])[CH:14]=2)[C:9](=O)[CH2:8][CH:7]1[CH3:20])=[O:5])[CH3:2].Cl.[NH2:22][OH:23].C([O-])(=O)C.[Na+].O>C(O)C>[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([O:17][CH3:18])=[C:13]([OH:16])[CH:14]=2)[C:9](=[N:22][OH:23])[CH2:8][CH:7]1[CH3:20])=[O:5])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 544378587-Hydroxy-6-methoxy-2-methyl-4-oxo-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester

Produkt 1

HCID 1363337157-Hydroxy-4-hydroxyimino-6-methoxy-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl esterAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 702EthanolLösungsmittel

Versuchsvorschrift

7-Hydroxy-6-methoxy-2-methyl-4-oxo-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester (5.10 g, 18.3 mmol) was dissolved in ethanol (100 mL), and hydroxylamine hydrochloride (3.81 g, 54.8 mmol) was added, followed by sodium acetate (3.74 g, 45.7 mmol). The mixture was heated at reflux for 2 h and then left to stand at room temperature overnight. Water (100 mL) was added, and the volatiles were removed in vacuo to give a yellow slurry. This slurry was filtered and washed with water to give the title compound as a fine powder (4.755 g, 89%).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 h
  3. waitleft
  4. customthe volatiles were removed in vacuo
  5. customto give a yellow slurry
  6. filtrationThis slurry was filtered
  7. washwashed with water

Quellen und Nachweise

ORD-Eintrag
ord-647611ff7a4b4f1f90e6434799ce3372
Quelldatensatz
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06362198B1

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