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

HRID 407085Notes

Reaction equation

HRID 407085 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

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

Workup

  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%)

Sources & evidence

ORD record
ord-85e9d28aaf6f49f691406e1a09f4fb7f
Source dataset
uspto-grants-2014_06
Patent number
US08754114B2

Reaction notes

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