2-Bromoaniline → Ethyl 8-bromo-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 1469736Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1469736
[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].C([O:11][CH:12]=[C:13]([C:19]([O-])=O)[C:14]([O:16][CH2:17][CH3:18])=[O:15])C>>[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:3]=1[N:4]=[CH:19][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:12]2[OH:11]

Komponenten

3

Edukt 2

HCID 119922-BromoanilineHCID 858292113-Ethoxy-2-ethoxycarbonylprop-2-enoate

Produkt 1

HCID 178469454Ethyl 8-bromo-4-oxo-1,4-dihydroquinoline-3-carboxylateAusbeute 80,8 %

Versuchsvorschrift

A solution of 2-bromoaniline (2.5 g, 14.62 mmol) and ethyl ethoxymethylenemalonate (3.16 g, 14.62 mmol) was heated at 100° C. for 3 h. Then the volatiles were removed by passing a stream of nitrogen and the molten mass was added slowly onto boiling diphenyl ether (10 mL) and the mixture was heated at reflux for 2 h. Then petroleum ether was added to the reaction mixture at rt and the precipitated solid was collected by filtration and dried to afford 3.5 g of the title product. 1H NMR (300 MHz, DMSO d6): δ 11.65 (br s, 1H), 8.45 (s, 1H), 8.17 (d, J=7.8 Hz, 1H), 8.05 (d, J=7.8 Hz, 1H), 7.39-7.34 (t, J=7.8 Hz, 1H), 4.26-4.19 (q, J=7.2, 14.1 Hz, 2H), 1.30-1.26 (t, J=6.9 Hz, 3H).

Aufarbeitung

  1. customThen the volatiles were removed
  2. additionthe molten mass was added slowly
  3. temperaturethe mixture was heated
  4. temperatureat reflux for 2 h
  5. additionThen petroleum ether was added to the reaction mixture at rt
  6. filtrationthe precipitated solid was collected by filtration
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-37e7c612a5ab47e88c2a3c047376d69d
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006257B2

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