Dimethylformamide → HCID 86613916、化合物

HRID 503988ノート

反応式

HRID 503988 の反応式
[H-].[Na+].CN(C=O)C.[O:8]=[C:9]1[C:18]([CH:19]=[O:20])=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10]1.[Cl:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Br)=[CH:24][CH:23]=1>C(OCC)(=O)C.O>[Cl:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][N:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:17]=[C:18]([CH:19]=[O:20])[C:9]2=[O:8])=[CH:24][CH:23]=1

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 5893342-Hydroxyquinoline-3-carbaldehyde

生成物 1

HCID 86613916HCID 86613916、化合物収率 74.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Sodium hydride (60% in oil) (1.3 g) was added at 0° C. to a DMF solution (50 ml) of 2-oxo-1,2-dihydroquinoline-3-carboxaldehyde (5.13 g), followed by stirring for 30 minutes. 4-chlorobenzyl bromide (7.0 g) was added, and the resulting mixture was stirred at room temperature overnight. Water was added to the reaction mixture, extraction with ethyl acetate was performed, and the extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:10→1:4). The purified product was recrystallized from a chloroform-diisopropyl ether mixed solvent to thereby obtain 6.57 g (yield: 72%) of 1-(4-chlorobenzyl)-2-oxo-1,2-dihydroquinoline-3-carboxaldehyde as a white powder.

後処理

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. dry with materialthe extract was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:10→1:4)
  5. customThe purified product was recrystallized from a chloroform-diisopropyl ether mixed solvent

出典と根拠

ORDレコード
ord-9e7a01cee91b48e1bf118eee2345eedd
出典データセット
uspto-grants-2010_08
特許番号
US07777038B2

反応ノート

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