3-Fluoro-4-nitrophenol → 6-Cyano-4-(3-fluoro-4-nitrophenoxy)-7-(2-methoxyethoxy)quinoline

HRID 1010080

Reaktionsgleichung

Reaktionsgleichung von HRID 1010080
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][O:17][CH3:18])=[C:9]([C:12]#[N:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[F:19][C:20]1[CH:21]=[C:22]([OH:29])[CH:23]=[CH:24][C:25]=1[N+:26]([O-:28])=[O:27]>ClC1C=CC=CC=1>[C:12]([C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH2:15][CH2:16][O:17][CH3:18])[N:5]=[CH:4][CH:3]=[C:2]2[O:29][C:22]1[CH:23]=[CH:24][C:25]([N+:26]([O-:28])=[O:27])=[C:20]([F:19])[CH:21]=1)#[N:13]

Komponenten

4

Edukt 2

HCID 5209483-Fluoro-4-nitrophenolHCID 226465224-Chloro-6-cyano-7-(2-methoxyethoxy)quinoline

Produkt 1

HCID 229365736-Cyano-4-(3-fluoro-4-nitrophenoxy)-7-(2-methoxyethoxy)quinolineAusbeute 62,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7964ChlorobenzeneLösungsmittel

Versuchsvorschrift

4-Chloro-6-cyano-7-(2-methoxyethoxy)quinoline (1.7 g) and 3-fluoro-4-nitrophenol (2.0 g) were suspended in chlorobenzene (20 ml), and the suspension was heated to reflux for 6 hours. After completion of the reaction, the solvent was distilled off, ethyl acetate was added, and a solid precipitated. The solid was filtered out and washed with ether, washed with 1N sodium hydroxide water and with water, and then dried to obtain 1.55 g of the title compound.

Aufarbeitung

  1. temperaturethe suspension was heated
  2. temperatureto reflux for 6 hours
  3. customAfter completion of the reaction
  4. distillationthe solvent was distilled off
  5. additionethyl acetate was added
  6. customa solid precipitated
  7. filtrationThe solid was filtered out
  8. washwashed with ether
  9. washwashed with 1N sodium hydroxide water and with water
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-374c2fc036ce453fb28777f8f00f4671
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973160B2

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