Phosphorus oxychloride → Ethyl 2-(4-(6-chloropyridazin-4-yl)phenyl)propanoate

HRID 407085노트

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HRID 407085 반응식
O=[C:2]1[NH:7][N:6]=[CH:5][C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([CH3:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:10][CH:9]=2)=[CH:3]1.P(Cl)(Cl)([Cl:23])=O>CN(C=O)C>[Cl:23][C:2]1[N:7]=[N:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([CH3:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:10][CH:9]=2)[CH:3]=1

참가 물질

4

반응물 2

HCID 24813Phosphorus oxychlorideHCID 67980170Ethyl 2-(4-(6-oxo-1,6-dihydropyridazin-4-yl)phenyl)propanoate

생성물 1

HCID 86667187Ethyl 2-(4-(6-chloropyridazin-4-yl)phenyl)propanoate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

A mixture of ethyl 2-[4-(6-oxo-1,6-dihydropyridazin-4-yl)phenyl]propanoate (0.48 g, 1.7 mmol) in phosphoryl chloride (5.0 mL) and DMF (50 μL) was stirred at 100° C. for 3 h. The solvent was removed and the residue was diluted with methylene chloride, washed with saturated NaHCO3, water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in methylene chloride (0-20%) to afford the desired product. LCMS (M+H)+: m/z=299.1

후처리

  1. customThe solvent was removed
  2. additionthe residue was diluted with methylene chloride
  3. washwashed with saturated NaHCO3, water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography on a silica gel column with ethyl acetate in methylene chloride (0-20%)

출처 및 근거

ORD 기록
ord-85e9d28aaf6f49f691406e1a09f4fb7f
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754114B2

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