Methanol → HCID 57793924, compound

HRID 1678402Notes

Reaction equation

HRID 1678402 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH3:14])=[N:12][NH:11][C:10](=[O:15])[C:9]=2[C:16]2[C:21]([F:22])=[CH:20][C:19](F)=[CH:18][C:17]=2[F:24])=[CH:4][CH:3]=1.[CH3:25][O-:26].[Na+].CO>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH3:14])=[N:12][NH:11][C:10](=[O:15])[C:9]=2[C:16]2[C:21]([F:22])=[CH:20][C:19]([O:26][CH3:25])=[CH:18][C:17]=2[F:24])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 10942334Sodium Methoxide2×HCID 57793906HCID 57793906, compound

Product 1

HCID 57793924HCID 57793924, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.35 g of 5-(4-chlorophenyl)-6-methyl-4-(2,4,6-trifluorophenyl)-2H-pyridazin-3-one, 0.96 g of sodium methoxide (28%-methanol solution) and 6 ml of methanol were mixed and stirred for 14 hours under reflux with heating. Next, to the reaction mixture was added 0.96 g of sodium methoxide (28% methanol solution), and stirred for 9 hours under reflux with heating. The reaction mixture was cooled to room temperature. Water was added to the reaction mixture, and extracted with ethyl acetate. The organic layer was washed with water, and dried over anhydrous magnesium sulfate, then, concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (elution solvent: hexane+tert-butyl methyl ether), to obtain 0.25 g of 5-(4-chlorophenyl)-4-(2,6-difluoro-4-methoxyphenyl)-6-methyl-2H-pyridazin-3-one.

Workup

  1. temperatureunder reflux
  2. temperaturewith heating
  3. stirringstirred for 9 hours
  4. temperatureunder reflux
  5. temperaturewith heating
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. washThe residue was subjected to silica gel column chromatography (elution solvent: hexane+tert-butyl methyl ether)

Sources & evidence

ORD record
ord-8faa4bb8e86e42a2a6829e21ae2ef23e
Source dataset
uspto-grants-2011_08
Patent number
US08008512B2

Reaction notes

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