Hydrochloric Acid → 3-acetyl-1-(4-iodo-2-methoxyphenyl)-5-methoxypyridazin-4(1H)-one

HRID 1528066

Reaction equation

HRID 1528066 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[C:12]([O:14][CH3:15])[C:11](=[O:16])[C:10]([C:17](N(OC)C)=[O:18])=[N:9]2)=[C:4]([O:23][CH3:24])[CH:3]=1.Cl.[CH2:26]1COCC1>>[C:17]([C:10]1[C:11](=[O:16])[C:12]([O:14][CH3:15])=[CH:13][N:8]([C:5]2[CH:6]=[CH:7][C:2]([I:1])=[CH:3][C:4]=2[O:23][CH3:24])[N:9]=1)(=[O:18])[CH3:26]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 594362051-(4-iodo-2-methoxyphenyl)-N,5-dimethoxy-N-methyl-4-oxo-1,4-dihydropyridazine-3-carboxamide

Product 1

HCID 866865553-acetyl-1-(4-iodo-2-methoxyphenyl)-5-methoxypyridazin-4(1H)-one

Procedure

To a solution of 1-(4-iodo-2-methoxyphenyl)-N,5-dimethoxy-N-methyl-4-oxo-1,4-dihydropyridazine-3-carboxamide (8.90 g) in THF (150 mL) was added dropwise 1M methylmagnesium bromide THF solution (30 mL) at −78° C., and the mixture was stirred for 20 min. To the reaction mixture was added 1M hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was washed with ethyl acetate, and recrystallized from methanol/water to give the title compound (5.12 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washThe residue was washed with ethyl acetate
  6. customrecrystallized from methanol/water

Sources & evidence

ORD record
ord-f72b8724a7504dfb83551c3d726fef6d
Source dataset
uspto-grants-2015_07
Patent number
US09090586B2

Linked notes

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