Sodium Methoxide → 6-Chloro-4-methoxy-3-(2-methylphenoxy)pyridazine

HRID 2424271Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[N:4][C:3]=1[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16].[CH3:17][O-:18].[Na+]>CO>[Cl:8][C:6]1[N:5]=[N:4][C:3]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])=[C:2]([O:18][CH3:17])[CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

In methanol (60 mL) was dissolved 3.00 g (11.8 mmol) of 4,6-dichloro-3-(2-methylphenoxy)pyridazine obtained in Example 1 (2), 1.00 g (17.6 mmol) of 95% sodium methoxide was added to the solution at room temperature and the mixture was stirred at 60° C. for 4 hours. Moreover, 1.00 g (17.6 mmol) of 95% sodium methoxide was further added and after stirring the mixture at 60° C. for 1 hour, it was allowed to stand at room temperature overnight. The reaction mixture was concentrated, ethyl acetate was added to the residue, and the mixture was successively washed with water and brine. After drying over anhydrous sodium sulfate, the solvent was removed, and the obtained residue was purified by silica gel column chromatography (eluted with hexane:ethyl acetate=4:1) to obtain 2.75 g (11.0 mmol, Yield: 93.2%) of 6-chloro-4-methoxy-3-(2-methylphenoxy)pyridazine.

Workup

additionwas added to the solution at room temperature
stirringafter stirring the mixture at 60° C. for 1 hour
waitto stand at room temperature overnight
concentrationThe reaction mixture was concentrated
additionethyl acetate was added to the residue
washthe mixture was successively washed with water and brine
dry with materialAfter drying over anhydrous sodium sulfate
customthe solvent was removed
customthe obtained residue was purified by silica gel column chromatography (eluted with hexane:ethyl acetate=4:1)

Sources & evidence

ORD record: ord-4eddf71ddf184cb3a7e3e3d306723552
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07964531B2

Reaction notes

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