Water → Ethyl 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-(1,2,4-triazol-1-ylmethyl)quinoline-3-carboxylate 1-oxide

HRID 862646ノート

反応式

HRID 862646 の反応式
[H-].[Na+].[NH:3]1[CH:7]=[N:6][CH:5]=[N:4]1.Cl[CH2:9][C:10]1[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:18]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[CH:26]=2)[C:17]2[C:12](=[CH:13][C:14]([O:37][CH3:38])=[C:15]([O:35][CH3:36])[CH:16]=2)[N+:11]=1[O-:39].O>CN(C)C=O>[CH3:36][O:35][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][C:14]=1[O:37][CH3:38])[N+:11]([O-:39])=[C:10]([CH2:9][N:3]1[CH:7]=[N:6][CH:5]=[N:4]1)[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:18]2[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[CH:26]=1

参加物

6

反応物 4

HCID 962WaterHCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 21851158Ethyl 2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate 1-oxide

生成物 1

HCID 22097599Ethyl 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-(1,2,4-triazol-1-ylmethyl)quinoline-3-carboxylate 1-oxide収率 50%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Oily sodium hydride (60%, 0.156 g) was added to a solution of 1H-1,2,4-triazole (0.27 g) in N,N-dimethylformamide (DMF)(20 ml), and the mixture was stirred at room temperature for 15 minutes. Then ethyl 2-chloromethyl-6,7-dimethoxy-4-(3,4-dimethoxyphenyl)quinoline-3-carboxylate 1-oxide (1.5 g) was added, and the mixture was stirred at 80° C. for 45 minutes. 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 residual oil was subjected to column chromatography on silica gel. The fractions eluted with chloroform/methanol (30/1, v/v) gave ethyl 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-(1,2,4-triazol-1-ylmethyl)quinoline-3-carboxylate 1-oxide (0.8 g, 50%) which was then recrystallized from dichloromethanehexane. Colorless prisms. mp. 221°-222° C.

後処理

  1. stirringthe mixture was stirred at 80° C. for 45 minutes
  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/methanol (30/1

出典と根拠

ORDレコード
ord-a2b86a6690ba4145bf61c639b3c7088f
出典データセット
uspto-grants-1998_02
特許番号
US05719157

反応ノート

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