Ammonium Chloride → 3-acetyl-5-methoxy-1-phenylpyridazin-4(1H)-one

HRID 333738Notes

Reaction equation

HRID 333738 reaction equation
CON(C)[C:4]([C:6]1[C:11](=[O:12])[C:10]([O:13][CH3:14])=[CH:9][N:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:7]=1)=[O:5].[CH3:22][Mg]Br.[Cl-].[NH4+]>O1CCCC1>[C:4]([C:6]1[C:11](=[O:12])[C:10]([O:13][CH3:14])=[CH:9][N:8]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:7]=1)(=[O:5])[CH3:22]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 89586475N,5-dimethoxy-N-methyl-4-oxo-1-phenyl-1,4-dihydropyridazine-3-carboxamideHCID 178418573HCID 178418573, compound

Product 1

HCID 895863493-acetyl-5-methoxy-1-phenylpyridazin-4(1H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-69 °C

Procedure

Under an argon atmosphere, to a stirring solution of N,5-dimethoxy-N-methyl-4-oxo-1-phenyl-1,4-dihydropyridazine-3-carboxamide (20 g) in tetrahydrofuran (1 L) was added dropwise, under cooling at −69° C., methyl magnesium bromide solution (1 M in THF, 138 mL). After stirring at −69° C. for 1.5 hr, a saturated aqueous ammonium chloride solution was added. Thereafter, the mixture was warmed to room temperature in 1.5 hr, and the reaction mixture was partitioned. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The aqueous layer was extracted with ethyl acetate, and the obtained extract was dried over anhydrous magnesium sulfate. The organic layer and the extract were combined, and concentrated under reduced pressure to dryness. The residue was purified by silica gel column chromatography (ethyl acetate/methanol) to give the title compound (13.22 g) as a pale-yellow solid.

Workup

  1. temperatureThereafter, the mixture was warmed to room temperature in 1.5 hr
  2. customthe reaction mixture was partitioned
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. extractionthe obtained extract
  7. dry with materialwas dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure to dryness
  9. customThe residue was purified by silica gel column chromatography (ethyl acetate/methanol)

Sources & evidence

ORD record
ord-2a6ac671287c42f0a1d13d92ee151e96
Source dataset
uspto-grants-2014_11
Patent number
US08883788B2

Reaction notes

Loading…