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 862626Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 862626
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-c997fb50a940499386409048538f7c2f
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05719157

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