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

HRID 407085ノート

反応式

HRID 407085 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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

後処理

  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%)

出典と根拠

ORDレコード
ord-85e9d28aaf6f49f691406e1a09f4fb7f
出典データセット
uspto-grants-2014_06
特許番号
US08754114B2

反応ノート

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