Methanol → ethyl 2-(N,N-diethylaminomethyl)-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate

HRID 266133

Reaktionsgleichung

Reaktionsgleichung von HRID 266133
Cl[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.[CH2:32]([NH:34][CH2:35][CH3:36])[CH3:33].CO>O>[CH2:32]([N:34]([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)[CH2:35][CH3:36])[CH3:33]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 8021DiethylamineHCID 10813243Ethyl 2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate

Produkt 1

HCID 9956900ethyl 2-(N,N-diethylaminomethyl)-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylateAusbeute 18 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of ethyl 2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate (4.0 g), diethylamine (1.28 g) and methanol (45 ml) was stirred at room temperature for 4 days. The reaction mixture was poured into water and extracted with dichloromethane. The dichloromethane layer was washed with water and dried over magnesium sulfate, and the solvent was evaporated. The residue was subjected to column chromatography on silica gel. The fractions eluted with ethyl acetate gave ethyl 2-(N,N-diethylaminomethyl)-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate (0.51 g, 18%). This compound was recrystallized from ethyl acetate-hexane. Colorless prisms, mp. 130°-131° C.

Aufarbeitung

  1. extractionextracted with dichloromethane
  2. washThe dichloromethane layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated
  5. washThe fractions eluted with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-7de866c9f4144e22bad95239e0e8cc41
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05650410

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