Diethylamine → ethyl 2-[2-(N,N-diethylamino)ethyl]-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate

HRID 266151Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 266151
Br[CH2:2][CH2:3][C:4]1[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:12]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=2)[C:11]2[C:6](=[CH:7][C:8]([O:31][CH3:32])=[C:9]([O:29][CH3:30])[CH:10]=2)[N:5]=1.[CH2:33]([NH:35][CH2:36][CH3:37])[CH3:34]>ClCCl>[CH2:33]([N:35]([CH2:2][CH2:3][C:4]1[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:12]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=2)[C:11]2[C:6](=[CH:7][C:8]([O:31][CH3:32])=[C:9]([O:29][CH3:30])[CH:10]=2)[N:5]=1)[CH2:36][CH3:37])[CH3:34]

Komponenten

4

Edukt 2

HCID 8021DiethylamineHCID 11799673Ethyl 2-(2-bromoethyl)-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate

Produkt 1

HCID 19032341ethyl 2-[2-(N,N-diethylamino)ethyl]-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylateAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of ethyl 2-(2-bromoethyl)-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate (0.45 g), diethylamine (0.326 g) and dichloromethane (10 ml) was stirred under reflux for 14 hours. The reaction mixture was washed with water and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel. The fractions eluted with chloroform-methanol (20:1, v/v) gave ethyl 2-[2-(N,N-diethylamino)ethyl]-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate (0.113 g, 26%). This compound was recrystallized from ethyl acetate - hexane. Colorless prisms, mp. 76°-78° C.

Aufarbeitung

  1. temperatureunder reflux for 14 hours
  2. washThe reaction mixture was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. washThe fractions eluted with chloroform-methanol (20:1

Quellen und Nachweise

ORD-Eintrag
ord-e6e2b11bb0f543aba34e94160a6f12f4
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05650410

Notizen zur Reaktion

Wird geladen…