Methane → 3-Methoxy-4-pyridin-2-ylaniline

HRID 746824

反応式

HRID 746824 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.CNNC.C>CO.[Fe](Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:6]=[CH:5][C:4]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)[NH2:9]

参加物

6

反応物 3

HCID 297MethaneHCID 13221,2-DimethylhydrazineHCID 219565262-(2-Methoxy-4-nitrophenyl)pyridine

生成物 1

HCID 219565203-Methoxy-4-pyridin-2-ylaniline

試薬・触媒・溶媒 2

HCID 24380Iron chloride (FeCl3)触媒HCID 887Methanol溶媒

反応条件

温度
65 °C

実験手順

To a solution of 2-(2-methoxy-4-nitrophenyl)pyridine (5.4 g, 23.3 mmol), dimethyl hydrazine (14 mL, 233 mmol), charcoal (0.7 g), in methanol (200 mL) was added iron trichloride (0.075 g, 0.46 mmol), then heated at 65° C. overnight. The reaction mixture was quenched with H2O (50 mL), then extracted with EtOAc (3×50 mL) and the combined organic extracts washed with brine. The organic phase was dried over Na2SO4 and concentrated in vacuo. The crude purified by liquid chromatography on silica (EtOAc/Hexane 3/7) to give 3-methoxy-4-pyridin-2-ylaniline.

後処理

  1. customThe reaction mixture was quenched with H2O (50 mL)
  2. extractionextracted with EtOAc (3×50 mL)
  3. washthe combined organic extracts washed with brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude purified by liquid chromatography on silica (EtOAc/Hexane 3/7)

出典と根拠

ORDレコード
ord-28f2fb9c9584446bb7f8ac57dcebcc5f
出典データセット
uspto-grants-2008_07
特許番号
US07393959B2

関連ノート

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