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3,6-Dichloropyridazine → 6-Chloro-N-methylpyridazin-3-amine

HRID 454824
Notes
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Reaction equation

HRID 454824 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]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 673313,6-DichloropyridazineHCID 57454252Monomethylamine methanol

Product 1

HCID 5885406-Chloro-N-methylpyridazin-3-amineYield 104.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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

  1. extractionwere extracted with ethyl acetate
  2. washThe recovered organic solution was washed with an aqueous solution of saturated sodium chloride
  3. customevaporated after a treatment with sodium sulfate
  4. customPurification

Sources & evidence

ORD record
ord-171ec25a3f954b868203a18a0508ed80
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08497260B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes