Phosphorus oxychloride → Methyl 4-chloro-6-oxo-1-phenyl-1,6-dihydropyridazine-3-carboxylate

HRID 1510571Notes

Reaction equation

HRID 1510571 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10](O)=[CH:9][C:8](=[O:12])[N:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:6]=1)=[O:4].P(Cl)(Cl)([Cl:21])=O>>[CH3:1][O:2][C:3]([C:5]1[C:10]([Cl:21])=[CH:9][C:8](=[O:12])[N:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:6]=1)=[O:4]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 54686161Methyl 1,6-dihydro-4-hydroxy-6-oxo-1-phenyl-3-pyridazinecarboxylate

Product 1

HCID 2784479Methyl 4-chloro-6-oxo-1-phenyl-1,6-dihydropyridazine-3-carboxylateYield 84%

Conditions

Temperature
85 °C

Procedure

A mixture of 4-hydroxy-6-oxo-1-phenyl-1,6-dihydropyridazine-3-carboxylic acid methyl ester (3.83 g, 15.6 mmol) and phosphorous oxychloride (50 mL) was heated to 85° C. After 20 hours, the reaction mixture was concentrated under reduced pressure. The resulting residue was quenched with water. The precipitate was filtered and dissolved in EtOAc, dried (MgSO4) and concentrated under reduced pressure to yield 3.44 g (84%) of desired product.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe resulting residue was quenched with water
  3. filtrationThe precipitate was filtered
  4. dissolutiondissolved in EtOAc
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-23e62a2e20de4ebdaf36ade5c86186d3
Source dataset
uspto-grants-2012_07
Patent number
US08211921B2

Reaction notes

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