Imidazole → 5-Imidazol-1-ylmethyl-quinolin-8-ol

HRID 23942

Reaktionsgleichung

Reaktionsgleichung von HRID 23942
Cl.Cl[CH2:3][C:4]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2.[NH:15]1[CH:19]=[CH:18][N:17]=[CH:16]1.C(N(C(C)C)CC)(C)C>C(Cl)(Cl)Cl>[N:15]1([CH2:3][C:4]2[CH:13]=[CH:12][C:11]([OH:14])=[C:10]3[C:5]=2[CH:6]=[CH:7][CH:8]=[N:9]3)[CH:19]=[CH:18][N:17]=[CH:16]1

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 81531DiisopropylethylamineHCID 122695968-Quinolinol, 5-(chloromethyl)-, hydrochloride (1:1)

Produkt 1

HCID 5941905-Imidazol-1-ylmethyl-quinolin-8-olAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A mixture of 5-chloromethyl-8-hydroxyquinoline hydrochloride (3.45 g; 15 mmol), imidazole (1.02 g; 15 mmol) and diisopropylethylamine (5.25 ml; 30 mmol) in CHCl3 (60 ml) was stirred for 24 h at room temperature and then for 3 h at 60° C. After cooling, the mixture was evaporated, washed with ethyl acetate (50 ml) and then hexane (50 ml). The residue was crystallized from a mixture of toluene and ethanol (abs.) to give 0.83 g (29%) of title product. M.p. 182° C.

Aufarbeitung

  1. waitfor 3 h at 60° C
  2. temperatureAfter cooling
  3. customthe mixture was evaporated
  4. washwashed with ethyl acetate (50 ml)
  5. customThe residue was crystallized from a mixture of toluene and ethanol (abs.)

Quellen und Nachweise

ORD-Eintrag
ord-1eb91e4390e4438fb90926e9ae38c271
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855711B1

Verknüpfte Notizen

Wird geladen…