Ethyl 2-iodomethyl-6,7-dimethoxy-4-(3,4-dimethoxyphenyl)quinoline-3-carboxylate → Ethyl 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-[(1-methyl-2-imidazolyl)oxymethyl]quinoline-3-carboxylate

HRID 1458916Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1458916
I[CH2:2][C:3]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=2)[C:10]2[C:5](=[CH:6][C:7]([O:30][CH3:31])=[C:8]([O:28][CH3:29])[CH:9]=2)[N:4]=1.[OH:32][C:33]1[N:34]([CH3:38])[CH:35]=[CH:36][N:37]=1>C(=O)([O-])[O-].[Ag+].[Ag+].C1C=CC=CC=1>[CH3:29][O:28][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][C:7]=1[O:30][CH3:31])[N:4]=[C:3]([CH2:2][O:32][C:33]1[N:34]([CH3:38])[CH:35]=[CH:36][N:37]=1)[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]2[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=1

Komponenten

5

Edukt 2

HCID 21851133Ethyl 2-iodomethyl-6,7-dimethoxy-4-(3,4-dimethoxyphenyl)quinoline-3-carboxylateHCID 178480601HCID 178480601, Verbindung

Produkt 1

HCID 21851189Ethyl 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-[(1-methyl-2-imidazolyl)oxymethyl]quinoline-3-carboxylateAusbeute 9,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 92796Silver carbonateKatalysatorHCID 241BenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of ethyl 2-iodomethyl-6,7-dimethoxy-4-(3,4-dimethoxyphenyl)quinoline-3-carboxylate (9.0 g), 2-hydroxy-1-methylimidazole (1.8 g), silver (I) carbonate (Ag2CO3)(5.1 g) and benzene (100 ml) was stirred at 50° C. for 18 hours. The insoluble solid was filtered off. The filtrate was washed with water and dried over magnesium sulfate, and the solvent was evaporated. The residual oil was subjected to column chromatography on silica gel. The fractions eluted with chloroform/ethyl acetate (5/1, v/v) gave ethyl 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-[(1-methyl-2-imidazolyl)oxymethyl]quinoline-3-carboxylate (0.8 g, 9%) which was then recrystallized from ethyl acetate-hexane.

Aufarbeitung

  1. filtrationThe insoluble solid was filtered off
  2. washThe filtrate was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated
  5. washThe fractions eluted with chloroform/ethyl acetate (5/1

Quellen und Nachweise

ORD-Eintrag
ord-62ea964fcb9a4560b5e0e68e8e718b23
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05852039

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