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

HRID 340218

반응식

HRID 340218 반응식
[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

참가 물질

6

반응물 2

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

생성물 1

HCID 187968643-Chloro-5-methoxypicolinonitrile

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
75 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-644b96ca644b477a93e2eaf644a3f724
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895577B2

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