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

HRID 1684583ノート

反応式

HRID 1684583 の反応式
[H-].[Na+].[NH:3]1[CH:7]=[N:6][CH:5]=[N:4]1.[C:8]([C:11]1[C:12]([CH2:35]Br)=[N:13][C:14]2[C:19]([C:20]=1[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=1)=[CH:18][C:17]([O:31][CH3:32])=[C:16]([O:33][CH3:34])[CH:15]=2)(=[O:10])[CH3:9].O>CN(C)C=O>[C:8]([C:11]1[C:12]([CH2:35][N:3]2[CH:7]=[N:6][CH:5]=[N:4]2)=[N:13][C:14]2[C:19]([C:20]=1[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=1)=[CH:18][C:17]([O:31][CH3:32])=[C:16]([O:33][CH3:34])[CH:15]=2)(=[O:10])[CH3:9]

参加物

6

反応物 4

HCID 962WaterHCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 190399053-Acetyl-2-bromomethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline

生成物 1

HCID 190398963-Acetyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-(1,2,4-triazol-1-ylmethyl)quinoline収率 43.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Oily sodium hydride (60%, 0.372 g) was added to a solution of 1H-1,2,4-triazole (0.594 g) in N,N-dimethylformamide (30 ml), and the mixture was stirred at room temperature for 15 minutes. Then, 3-acetyl-2-bromomethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline (3.3 g) was added, and the mixture was stirred at 80° C. for 40 minutes. The reaction mixture was poured into water, and extracted with ethyl acetate. The ethyl acetate layer 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-4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-(1,2,4-triazol-1-ylmethyl)quinoline (1.4 g, 42%). This compound was recrystallized from ethanol to give colorless prisms, mp. 180°-181° C.

後処理

  1. stirringthe mixture was stirred at 80° C. for 40 minutes
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated
  6. washThe fractions eluted with chloroform

出典と根拠

ORDレコード
ord-e91eae859bde4549861b0e8a38176a3c
出典データセット
uspto-grants-1997_06
特許番号
US05641788

反応ノート

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