Sodium Hydroxide → 4-Bromo-7-chloro-3-(4-chloro-benzenesulfonyl)-quinoline

HRID 561045Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 561045
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](O)=[C:7]([S:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.O(Br)[Br:24].[P+5].[OH-].[Na+]>C(Cl)(Cl)Cl.C(N(CC)CC)C.O>[Br:24][C:6]1[C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]=[CH:8][C:7]=1[S:12]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13]

Komponenten

7

Edukt 3

HCID 14798Sodium HydroxideHCID 178419731HCID 178419731, VerbindungHCID 178527342HCID 178527342, Verbindung

Produkt 1

HCID 670001544-Bromo-7-chloro-3-(4-chloro-benzenesulfonyl)-quinolineAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A mixture of 7-chloro-3-(4-chloro-benzenesulfonyl)-quinolin-4-ol (0.5 g, 1.41 mmol) and phosphorus(V) oxybromide (1.2 g, 4.2 mmol) in chloroform (30 ml) and triethylamine (1 ml) was refluxed for 6 hours. The reaction mixture was diluted with water (30 ml) and the pH was adjusted to 10 with aqueous sodium hydroxide solution. The organic layer was separated, dried over sodium sulfate, filtered, and concentrated in vacuo. The obtained crude product was purified by crystallization from diethyl ether to obtain 0.45 g of the title compound in 77% yield.

Aufarbeitung

  1. temperaturewas refluxed for 6 hours
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe obtained crude product
  7. customwas purified by crystallization from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-04010ee87e9b40d597c275db2c18b120
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063220B2

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