Pyridine → N-(4-chloropyridin-3-yl)-2-nitrobenzamide

HRID 44239

反応式

HRID 44239 の反応式
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[Cl:8].[N+:9]([C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14](Cl)=[O:15])([O-:11])=[O:10].N1C=CC=CC=1>O1CCCC1>[Cl:8][C:7]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[NH:1][C:14](=[O:15])[C:13]1[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=1[N+:9]([O-:11])=[O:10]

参加物

5

反応物 3

HCID 1049PyridineHCID 118752-Nitrobenzoyl chlorideHCID 5819323-Amino-4-chloropyridine

生成物 1

HCID 67434091N-(4-chloropyridin-3-yl)-2-nitrobenzamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 3-amino-4-chloropyridine (5 g, 39 mmol), 2-nitrobenzoyl chloride (5.1 mL, 39 mmol) and pyridine (11 mL) in tetrahydrofuran (50 mL) was stirred for 20 hours. The reaction mixture was partitioned between water (200 mL) and dichloromethane (600 mL). The phases were separated and the organic phase was washed with water (150 mL) then brine (150 mL). The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography (SiO2, 10% ethyl acetate in dichloromethane). The N-(4-chloropyridin-3-yl)-2-nitrobenzamide was obtained as a brown solid (2.0 g). LCMS [M+H]: 279.

後処理

  1. customThe reaction mixture was partitioned between water (200 mL) and dichloromethane (600 mL)
  2. customThe phases were separated
  3. washthe organic phase was washed with water (150 mL)
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography (SiO2, 10% ethyl acetate in dichloromethane)

出典と根拠

ORDレコード
ord-fa642dc6671442b284ddd57048d9fa5b
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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