Diethylamine → 3-acetyl-2-(N,N-diethylaminomethyl)-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline

HRID 1684581Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1684581
[C:1]([C:4]1[C:5]([CH2:28]Br)=[N:6][C:7]2[C:12]([C:13]=1[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=1)=[CH:11][C:10]([O:24][CH3:25])=[C:9]([O:26][CH3:27])[CH:8]=2)(=[O:3])[CH3:2].[CH2:30]([NH:32][CH2:33][CH3:34])[CH3:31]>ClCCl>[C:1]([C:4]1[C:5]([CH2:28][N:32]([CH2:33][CH3:34])[CH2:30][CH3:31])=[N:6][C:7]2[C:12]([C:13]=1[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=1)=[CH:11][C:10]([O:24][CH3:25])=[C:9]([O:26][CH3:27])[CH:8]=2)(=[O:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 8021DiethylamineHCID 190399053-Acetyl-2-bromomethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline

Produkt 1

HCID 98900803-acetyl-2-(N,N-diethylaminomethyl)-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinolineAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 3-acetyl-2-bromomethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline (3.0 g), diethylamine (4.76 g) and dichloromethane (50 ml) was stirred under reflux for 14 hours. The reaction mixture was washed with water, 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 3-acetyl-2-(N,N-diethylaminomethyl)-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline (2.07 g, 73%). This compound was recrystallized from ethyl acetate-hexane to give colorless prisms, mp. 146°-148° 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
  5. washThe fractions eluted with chloroform

Quellen und Nachweise

ORD-Eintrag
ord-f54f94bb90f44c4cac23219629d09037
Quelldatensatz
uspto-grants-1997_06
Patentnummer
US05641788

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