4-Chloroaniline → HCID 18372708, Verbindung

HRID 382862Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 382862
[Br:1][C:2]1[CH:11]=[C:10]([C:12]([OH:14])=O)[C:9]([OH:15])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[Cl:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1.P(Cl)(Cl)Cl>O>[Br:1][C:2]1[CH:11]=[C:10]([C:12]([NH:21][C:20]2[CH:22]=[CH:23][C:17]([Cl:16])=[CH:18][CH:19]=2)=[O:14])[C:9]([OH:15])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Komponenten

5

Edukt 3

HCID 78124-ChloroanilineHCID 24387Phosphorus trichlorideHCID 145347685-Bromo-8-hydroxyquinoline-7-carboxylic acid

Produkt 1

HCID 18372708HCID 18372708, VerbindungAusbeute 52,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 5-bromo-8-hydroxyquinoline-7-carboxylic acid (2.68 g) of Preparation 2 and 4-chloroaniline (1.28 g) in 250 mL xylenes is heated to reflux. To this is added dropwise PCl3 (0.69 g). Refluxing is continued overnight. The reaction is then cooled and water is added to destroy excess PCl3. The resulting solid is collected, washed with water and dried. The crude product is recrystallized from EtOAc/hexanes to yield 1.97 g of the title product as an orange solid.

Aufarbeitung

  1. temperatureis heated to reflux
  2. temperatureRefluxing
  3. temperatureThe reaction is then cooled
  4. customto destroy excess PCl3
  5. customThe resulting solid is collected
  6. washwashed with water
  7. customdried
  8. customThe crude product is recrystallized from EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-ea4c18fb2e574ae3a40982b872b6f2fc
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06310211B1

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