Methanol → 4-Chloro-5-methoxy-2-methyl-2,3-dihydropyridazin-3-one

HRID 2194418Notes

Reaction equation

HRID 2194418 reaction equation
[Na].[Cl:2][C:3]1[C:4](=[O:11])[N:5]([CH3:10])[N:6]=[CH:7][C:8]=1Cl.[Cl-].[NH4+].[CH3:14][OH:15]>>[Cl:2][C:3]1[C:4](=[O:11])[N:5]([CH3:10])[N:6]=[CH:7][C:8]=1[O:15][CH3:14]

Participants

5

Reactant 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 1204623(2H)-Pyridazinone, 4,5-dichloro-2-methyl-HCID 5360545Sodium

Product 1

HCID 27749384-Chloro-5-methoxy-2-methyl-2,3-dihydropyridazin-3-oneYield 97%

Procedure

Sodium metal (613 mg, 26.7 at-g) were dissolved in 35 ml of methanol. To this solution were added 4.15 g (23.18 mmol) of 4,5-dichloro-2-methyl-2H-pyridazin-3-one in four portions over 5 min. After stirring the suspension for 4 h at room temperature, the solution was neutralized by addition of 1 ml sat. ammonium chloride solution and concentrated in vaccuo. The residue was taken up in 100 ml of ethyl acetate, washed twice with water, drie over magnesium sulfate and concentrated in vaccuo to yield 3.94 g (22.6 mmol, 97%) of the title compound as a crystalline white solid, MS: 175.2, 177.0 (M+H+).

Workup

  1. concentrationconcentrated in vaccuo
  2. washwashed twice with water, drie over magnesium sulfate
  3. concentrationconcentrated in vaccuo

Sources & evidence

ORD record
ord-0cde91357dbd4965a84f5c2611cfb26b
Source dataset
uspto-grants-2012_12
Patent number
US08334287B2

Reaction notes

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