Triethylamine → 3-Bromo-7-chloro-N-(1-hydroxycyclohexylmethyl)-4-quinolinamine

HRID 2165845Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2165845
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][CH2:13][C:14]3([OH:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[Br:21]Br.[OH-].[Na+].C(N(CC)CC)C>C(O)(=O)C.O>[Br:21][C:7]1[CH:8]=[N:9][C:10]2[C:5]([C:6]=1[NH:12][CH2:13][C:14]1([OH:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[CH:4][CH:3]=[C:2]([Cl:1])[CH:11]=2

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 24408BromineHCID 142092337-Chloro-N-[(1-hydroxycyclohexyl)methyl]-4-quinolinamine

Produkt 1

HCID 142092443-Bromo-7-chloro-N-(1-hydroxycyclohexylmethyl)-4-quinolinamineAusbeute 49,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 11.2 g of 7-chloro-N-(1-hydroxycyclohexylmethyl)-4-quinolinamine in 130 ml of glacial acetic acid was stirred at room temperature and 6.15 g of bromine was added dropwise. The product precipitated from the solution as the hydrobromide salt and was isolated by filtration. The solid was then suspended in water and basified with sodium hydroxide. After two hours of stirring, the solid was collected by filtration. By combustion analysis, the product proved to be a hemi-hydrobromide salt, and therefore it was necessary to dissolve the solid in methanol and 1 equivalent of trietylamine with heating. A solid resulted which was recrystallized from ethanol to give 7 g of crystalline solid with melting point of 151°-154° C.

Aufarbeitung

  1. customThe product precipitated from the solution as the hydrobromide salt
  2. customwas isolated by filtration
  3. filtrationthe solid was collected by filtration
  4. dissolutionto dissolve the solid in methanol
  5. customA solid resulted which
  6. customwas recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-185e18e3081d4004a94bbe8566882b10
Quelldatensatz
uspto-grants-1990_07
Patentnummer
US04942168

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