3,5-Dichloro-2-cyanopyridine → 3-Chloro-5-methoxypicolinonitrile

HRID 340218

反応式

HRID 340218 の反応式
[Cl:1][C:2]1[C:3]([C:9]#[N:10])=[N:4][CH:5]=[C:6](Cl)[CH:7]=1.[CH3:11][O-:12].[Na+]>CN(C)C=O.C(OCC)(=O)C.O>[Cl:1][C:2]1[C:3]([C:9]#[N:10])=[N:4][CH:5]=[C:6]([O:12][CH3:11])[CH:7]=1

参加物

6

反応物 2

HCID 27696993,5-Dichloro-2-cyanopyridineHCID 10942334Sodium Methoxide

生成物 1

HCID 187968643-Chloro-5-methoxypicolinonitrile

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
75 °C

実験手順

To a solution of 3,5-dichloropicolinonitrile (1.0 eq.) in dimethyl formamide (DMF) (0.5 M) was added sodium methoxide (1.5 eq.) and heated to 75° C. After stirring for 14 hours, the reaction was diluted with ethyl acetate and water. The organic layer was washed with saturated aqueous NaHCO3 three times, water twice, dried over anhydrous MgSO4, and concentrated en vacuo. The crude residue was purified by a COMBIFLASH® system (ISCO) using 15% ethyl acetate in hexane to give a mixture of two methoxy regioisomers, one of which was the desired product. The mixture was carried onto the next step without further purification.

後処理

  1. washThe organic layer was washed with saturated aqueous NaHCO3 three times, water twice
  2. dry with materialdried over anhydrous MgSO4
  3. concentrationconcentrated en vacuo
  4. customThe crude residue was purified by a COMBIFLASH® system (ISCO)
  5. customto give
  6. additiona mixture of two methoxy regioisomers, one of which

出典と根拠

ORDレコード
ord-644b96ca644b477a93e2eaf644a3f724
出典データセット
uspto-grants-2014_11
特許番号
US08895577B2

関連ノート

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