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

HRID 1510498Notes

Reaction equation

HRID 1510498 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%

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 healed 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. customwas healed to 85° C
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe resulting residue was quenched with water
  4. filtrationThe precipitate was filtered
  5. dissolutiondissolved in EtOAc
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f49e23357a354f51a36a8e12592c22c2
Source dataset
uspto-grants-2012_07
Patent number
US08211920B2

Reaction notes

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