Ethanol → ethyl 2-(N-cyclohexyl-N-methylaminomethyl)-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate

HRID 266141

Reaktionsgleichung

Reaktionsgleichung von HRID 266141
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.[CH3:32][NH:33][CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1.C(O)C>O>[CH:34]1([N:33]([CH2:2][C:3]2[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=3)[C:10]3[C:5](=[CH:6][C:7]([O:30][CH3:31])=[C:8]([O:28][CH3:29])[CH:9]=3)[N:4]=2)[CH3:32])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1

Komponenten

5

Edukt 3

HCID 702EthanolHCID 7514N-MethylcyclohexylamineHCID 10813243Ethyl 2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate

Produkt 1

HCID 22097632ethyl 2-(N-cyclohexyl-N-methylaminomethyl)-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylateAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of ethyl 2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate (3.0 g), N-methyl-N-cyclohexylamine (2.28 g) and ethanol (45 ml) was stirred under reflux for 6 hours. 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 chloroform gave ethyl 2-(N-cyclohexyl-N-methylaminomethyl)-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate (2.80 g, 80%). This compound was recrystallized from ethanol. Colorless prisms, mp. 172°-174° C.

Aufarbeitung

  1. temperatureunder reflux for 6 hours
  2. extractionextracted with dichloromethane
  3. washThe dichloromethane layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated
  6. washThe fractions eluted with chloroform

Quellen und Nachweise

ORD-Eintrag
ord-66880303f16742988c59849cfb97c75c
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05650410

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