Sodium Methoxide → 5-chloro-4-methoxy-2-methoxymethyl-2H-pyridazin-3-one

HRID 1186888Notes

Reaction equation

HRID 1186888 reaction equation
Cl[C:2]1[C:3](=[O:12])[N:4]([CH2:9][O:10][CH3:11])[N:5]=[CH:6][C:7]=1[Cl:8].[CH3:13][O-:14].[Na+]>O1CCOCC1>[Cl:8][C:7]1[CH:6]=[N:5][N:4]([CH2:9][O:10][CH3:11])[C:3](=[O:12])[C:2]=1[O:14][CH3:13]

Participants

4

Reactant 2

HCID 10942334Sodium Methoxide2×HCID 123518344,5-dichloro-2-methoxymethyl-2H-pyridazin-3-one

Product 1

HCID 670109185-chloro-4-methoxy-2-methoxymethyl-2H-pyridazin-3-oneYield 93.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 4,5-dichloro-2-methoxymethyl-2H-pyridazin-3one (1.00 g, 4.78 mmol) in 1,4-dioxane (25 mL) at room temperature was added sodium methoxide (271 mg, 5.02 mmol). After 19 h, the reaction was added additional 271 mg of sodium methoxide and was continued to stir for 6 h. The reaction was filtered and the filtrate was concentrated to give 915 mg (93% crude) 5-chloro-4-methoxy-2-methoxymethyl-2H-pyridazin-3-one.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-880fe59b47984c9699ee9d3e0e6a2021
Source dataset
uspto-grants-2014_03
Patent number
US08673916B2

Reaction notes

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