Phosphorus oxychloride → 4-Chloro-1,5-dimethyl-6-oxo-1,6-dihydropyridazine-3-carboxylic acid

HRID 2068912Notes

Reaction equation

HRID 2068912 reaction equation
O[C:2]1[C:3]([C:11]([OH:13])=[O:12])=[N:4][N:5]([CH3:10])[C:6](=[O:9])[C:7]=1[CH3:8].O=P(Cl)(Cl)[Cl:16]>>[Cl:16][C:2]1[C:3]([C:11]([OH:13])=[O:12])=[N:4][N:5]([CH3:10])[C:6](=[O:9])[C:7]=1[CH3:8]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 574421684-Hydroxy-1,5-dimethyl-6-oxo-1,6-dihydropyridazine-3-carboxylic acid

Product 1

HCID 666732574-Chloro-1,5-dimethyl-6-oxo-1,6-dihydropyridazine-3-carboxylic acidYield 60%

Conditions

Temperature
85 °C

Procedure

A mixture of 4-hydroxy-1,5-dimethyl-6-oxo-1,6-dihydropyridazine-3-carboxylic acid (876 mg, 4.76 mmol) and POCl3 (4.5 mL) was heated for 24 hours at 85° C. POCl3 was removed under reduced pressure. The crude material was quenched with ice. The reaction mixture was stirred for 1 hour at room temperature. After removing solids by filtration, the aqueous filtrate was extracted with EtOAc (3×). The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure to give. The recovered material was combined with the solids previously isolated and triturated with ether to afford 577 mg (60%) of the desired product.

Workup

  1. customPOCl3 was removed under reduced pressure
  2. customThe crude material was quenched with ice
  3. customAfter removing solids
  4. filtrationby filtration
  5. extractionthe aqueous filtrate was extracted with EtOAc (3×)
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto give
  10. custompreviously isolated
  11. customtriturated with ether

Sources & evidence

ORD record
ord-eb6289202d1f4788a51f38c3d4c10b69
Source dataset
uspto-grants-2012_10
Patent number
US08299076B2

Reaction notes

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