Dimethylformamide → 1-(4-Carbomethoxybenzyl)-8-methoxy-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde

HRID 504011ノート

反応式

HRID 504011 の反応式
[H-].[Na+].CN(C=O)C.[CH3:8][O:9][C:10]1[C:19]2[NH:18][C:17](=[O:20])[CH2:16][CH2:15][C:14]=2[C:13]([CH:21]=[O:22])=[CH:12][CH:11]=1.[CH3:23][O:24][C:25]([C:27]1[CH:32]=[CH:31][C:30]([CH2:33]Br)=[CH:29][CH:28]=1)=[O:26]>C(OCC)(=O)C.O>[C:25]([C:27]1[CH:32]=[CH:31][C:30]([CH2:33][N:18]2[C:19]3[C:10]([O:9][CH3:8])=[CH:11][CH:12]=[C:13]([CH:21]=[O:22])[C:14]=3[CH2:15][CH2:16][C:17]2=[O:20])=[CH:29][CH:28]=1)([O:24][CH3:23])=[O:26]

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 256687Methyl 4-(bromomethyl)benzoateHCID 859802658-Methoxy-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde

生成物 1

HCID 866139251-(4-Carbomethoxybenzyl)-8-methoxy-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde収率 62.5%

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) (2.87 g) was added at 0° C. to a DMF solution (100 ml) of 8-methoxy-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde (13.4 g), followed by stirring for 30 minutes. Methyl 4-bromomethyl benzoate (18.0 g) was added, and the resulting mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and extraction with ethyl acetate was performed. The extract was washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:4→1:2). The purified product was recrystallized from a chloroform-diisopropyl ether mixed solvent to thereby obtain 14.43 g (yield: 62%) of 1-(4-carbomethoxybenzyl)-8-methoxy-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde as a white powder.

後処理

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

出典と根拠

ORDレコード
ord-ab9498d3839c41a79fd0d3412c656a01
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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