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

HRID 221855Notes

Reaction equation

HRID 221855 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-fee984a2bd694c61b573d3ff28a7338e
Source dataset
uspto-grants-2012_06
Patent number
US08207168B2

Reaction notes

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