N-Methylaniline → 5-(3,4-dimethoxybenzoyl)-2-(N-methylanilino)pyridine

HRID 1031500ノート

反応式

HRID 1031500 の反応式
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H-].[Na+].Cl[C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:29])[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=2)=[CH:14][N:13]=1>CN(C)C=O>[CH3:28][O:27][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][C:22]=1[O:25][CH3:26])[C:18]([C:15]1[CH:16]=[CH:17][C:12]([N:2]([CH3:1])[C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[N:13][CH:14]=1)=[O:29]

参加物

5

反応物 3

HCID 7515N-MethylanilineHCID 24758Sodium hydrideHCID 148232212-Chloro-5-(3,4-dimethoxybenzoyl)pyridine

生成物 1

HCID 148788655-(3,4-dimethoxybenzoyl)-2-(N-methylanilino)pyridine収率 31.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

In dimethylformamide (30 ml) was dissolved N-methylaniline (1.2 g). To the solution was added 60% sodium hydride (dispersion in praraffin) (150 mg), and the mixture was stirred for 30 minutes. Then there was added 2-chloro-5-(3,4-dimethoxybenzoyl)pyridine (500 mg). The mixture was stirred for 4 hours at 90° C. The reaction mixture was poured into ice-water, which was subjected to extraction with dichloromethane. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was purified by means of a silica gel column chromatography (eluent: n-hexane +ethyl acetate=2:1) to obtain 5-(3,4-dimethoxybenzo-yl)-2-(N-methylanilino)pyridine (200 mg) as an oil.

後処理

  1. stirringThe mixture was stirred for 4 hours at 90° C
  2. extractionwas subjected to extraction with dichloromethane
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe concentrate was purified by means of a silica gel column chromatography (eluent: n-hexane +ethyl acetate=2:1)

出典と根拠

ORDレコード
ord-3cbcb446ba4046c6aa34102311824f6f
出典データセット
uspto-grants-1990_09
特許番号
US04954497

反応ノート

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