3,6-Dichloropyridazine → 6-Chloro-N-methylpyridazin-3-amine
Reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][CH:7]=1.CO.[CH3:11][NH2:12]>O>[CH3:11][NH:12][C:5]1[N:4]=[N:3][C:2]([Cl:1])=[CH:7][CH:6]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
3,6-Dichloropyridazine (107, 500 mg, 3.36 mmol) was slowly added to a 2.0 M methylamine methanol solution (NH2Me in MeOH, 5 mL, 10 mmol) and stirred at room temperature for 24 hours. Water was added to the reaction mixture, and organic compounds were extracted with ethyl acetate. The recovered organic solution was washed with an aqueous solution of saturated sodium chloride and evaporated after a treatment with sodium sulfate. Purification was performed by column chromatograph to give the target compound 3-(N-monomethylamino)-6-chloropyridazine (108e, 505 mg, 88%) as a white solid.
Workup
- extractionwere extracted with ethyl acetate
- washThe recovered organic solution was washed with an aqueous solution of saturated sodium chloride
- customevaporated after a treatment with sodium sulfate
- customPurification
Sources & evidence
- ORD record
- ord-171ec25a3f954b868203a18a0508ed80
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08497260B2
Reaction notes
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