2-Benzyl-4,5-dichloro-2,3-dihydropyridazin-3-one → 2-Benzyl-4-chloro-5-methoxypyridazin-3(2h)-one

HRID 2224266Notes

Reaction equation

HRID 2224266 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]([Cl:15])=[C:11](Cl)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][O-:18].[Na+]>CO.C(Cl)Cl>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]([Cl:15])=[C:11]([O:18][CH3:17])[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7224382-Benzyl-4,5-dichloro-2,3-dihydropyridazin-3-oneHCID 10942334Sodium Methoxide

Product 1

HCID 7370152-Benzyl-4-chloro-5-methoxypyridazin-3(2h)-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-benzyl-4,5-dichloro-2H-pyridazine-3-one (22.31 g, 87.47 mmol), prepared as described in Example 244A, in dry MeOH (175 mL) at 0° C., was added dropwise a solution of sodium methoxide in methanol (25% weight in MeOH, 25 mL). The mixture was slowly warmed up to room temperature and stirred for 18 h. The reaction mixture was diluted with methylene chloride (200 mL) and filtered. The filtrate was concentrated to afford the title compound, 2-benzyl-4-chloro-5-methoxypyridazin-3(2H)-one (22.2 g) which was >95% pure as judged by HPLC and was used in the next reaction, Example 354B, without further purification.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-dc4920055d6943cfbcf8e8ea451d75fe
Source dataset
uspto-grants-2008_05
Patent number
US07378418B2

Reaction notes

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