Methanol → 6-(3-fluoro-4-methylphenyl)-4-methoxycarbonyl-2H-pyridazin-3-one

HRID 1348690

Reaction equation

HRID 1348690 reaction equation
[C:1]([C:4]1[C:5](=[O:18])[NH:6][N:7]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]([F:17])[CH:11]=2)[CH:9]=1)([OH:3])=[O:2].S(Cl)(Cl)=O.[CH3:23]O>>[F:17][C:12]1[CH:11]=[C:10]([C:8]2[CH:9]=[C:4]([C:1]([O:3][CH3:23])=[O:2])[C:5](=[O:18])[NH:6][N:7]=2)[CH:15]=[CH:14][C:13]=1[CH3:16]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 219915554-carboxy-6-(3-fluoro-4-methylphenyl)-2H-pyridazin-3-one

Product 1

HCID 219914756-(3-fluoro-4-methylphenyl)-4-methoxycarbonyl-2H-pyridazin-3-oneYield 92.7%

Conditions

Temperature
80 °C

Procedure

To an ice-cold suspension of 4-carboxy-6-(3-fluoro-4-methylphenyl)-2H-pyridazin-3-one (5.50 g, 22.2 mmol) in methanol (100 mL) was added dropwise thionyl chloride (2.72 g, 24.4 mmol), and the mixture was stirred at 80° C. for 8 hours. The temperature of the reaction mixture was allowed to drop back to room temperature, and the solvent was distilled off under reduced pressure. Water was added to the ice-cold residue. The precipitate was collected by filtration, washed with water and dried to yield the title compound as pale yellow fine-needles (5.43 g, 92.7%).

Workup

  1. customto drop back to room temperature
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionWater was added to the ice-cold residue
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-3685eafec1a240aea0b9781fd828e42c
Source dataset
uspto-grants-2007_05
Patent number
US07211577B2

Linked notes

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