Pyridine → N-(2-chloropyridin-3-yl)-5-methyl-2-nitrobenzamide

HRID 44236

反応式

HRID 44236 の反応式
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7](Cl)=[O:8].[Cl:14][C:15]1[C:20]([NH2:21])=[CH:19][CH:18]=[CH:17][N:16]=1.N1C=CC=CC=1>O1CCCC1.O>[Cl:14][C:15]1[C:20]([NH:21][C:7](=[O:8])[C:6]2[CH:10]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]=2[N+:11]([O-:13])=[O:12])=[CH:19][CH:18]=[CH:17][N:16]=1

参加物

6

反応物 3

HCID 1049PyridineHCID 805282-Chloro-3-pyridylamineHCID 30160135-Methyl-2-nitrobenzoyl chloride

生成物 1

HCID 3440161N-(2-chloropyridin-3-yl)-5-methyl-2-nitrobenzamide収率 98.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of 5-methyl-2-nitrobenzoyl chloride (3.77 g, 18.9 mmol) in tetrahydrofuran (25 mL) was treated with a solution consisting of 2-chloropyridin-3-amine (2.6 g, 20.22 mmol), pyridine (6 mL) and tetrahydrofuran (15 mL). The reaction mixture was stirred for 2 hours then diluted with water (150 mL) and extracted with dichloromethane (3×70 mL). The combined organic extracts were washed with saturated aqueous sodium bicarbonate (100 mL) and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford N-(2-chloropyridin-3-yl)-5-methyl-2-nitrobenzamide (5.44 g) that was used without further purification. LCMS [M+H]: 292.

後処理

  1. extractionextracted with dichloromethane (3×70 mL)
  2. washThe combined organic extracts were washed with saturated aqueous sodium bicarbonate (100 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-8de85d599504467eb920c5fc0f296886
出典データセット
uspto-grants-2013_09
特許番号
US08541407B2

関連ノート

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