Diphenyl Ether → HCID 178469501, Verbindung

HRID 852981Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 852981
C(O[C:4](=[O:20])[C:5](=[CH:11][NH:12][C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.C1(OC2C=CC=CC=2)C=CC=CC=1>C(O)C>[CH2:9]([O:8][C:6]([C:5]1[CH:11]=[N:12][C:13]2[C:14]([C:4]=1[OH:20])=[CH:15][C:16]([Br:19])=[CH:17][CH:18]=2)=[O:7])[CH3:10]

Komponenten

4

Edukt 2

HCID 7583Diphenyl EtherHCID 1591151Diethyl 2-((4-bromophenylamino)methylene)malonate

Produkt 1

HCID 178469501HCID 178469501, VerbindungAusbeute 97,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

The solid 2-[(4-bromo-phenylamino)-methylene]-malonic acid diethyl ester (157 g, 458.8 mmol) was added to a hot diphenyl ether (260 g) and the mixture was heated to reflux for 5 h to afford a brown suspension. Then, the mixture was cooled to 100° C. and diluted with ethanol (˜200 mL). This suspension was refluxed for 10 min and then cooled to room temperature. The solids were collected by filtration and washed with diethyl ether. After drying in air, 132.59 g (97.6% yield) of 6-bromo-4-hydroxy-quinoline-3-carboxylic acid ethyl ester was isolated as a white solid: EI-HRMS m/e calcd for C8H6N2O (M+) 146.0480, found 146.0478.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 5 h
  3. customto afford a brown suspension
  4. temperatureThis suspension was refluxed for 10 min
  5. temperaturecooled to room temperature
  6. filtrationThe solids were collected by filtration
  7. washwashed with diethyl ether
  8. customAfter drying in air

Quellen und Nachweise

ORD-Eintrag
ord-fa3ace34ba8046bbb9d46ddafd87c01d
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07253285B2

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