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Methylhydrazine → 3-Chloro-6-(1-methylhydrazinyl)pyridazine

HRID 39304
Notes
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Reaction equation

HRID 39304 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][CH:7]=1.[CH3:9][NH:10][NH2:11]>>[Cl:1][C:2]1[N:3]=[N:4][C:5]([N:10]([CH3:9])[NH2:11])=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 6061Methylhydrazine2×HCID 673313,6-Dichloropyridazine

Product 1

HCID 27358153-Chloro-6-(1-methylhydrazinyl)pyridazineYield 53.8%

Procedure

3,6-Dichloro-pyridazine (1 g, 6/5 mmol) was placed in a flask fitted with a water condenser and methylhydrazine (1.31 mL, 25 mmol) was added dropwise. An immediate exotherm was observed and methylhydrazine begins to reflux. When the reaction had subsided, the mixture was left for 16 hours, and the excess methylhydrazine was removed under reduced pressure. The cooled residue was stirred with aqueous sodium hydroxide solution (20 ml of 20%), and the resulting solution was extracted with ether (6×100 ml). The combined extracts were dried (K2CO3) and concentrated to give 427 mg of N-(6-Chloro-pyridazin-3-yl)-N-methyl-hydrazine.

Workup

  1. customfitted with a water condenser
  2. temperatureto reflux
On this pageParticipantsProcedureWorkupSources & evidenceReaction notes
  • customthe excess methylhydrazine was removed under reduced pressure
  • extractionthe resulting solution was extracted with ether (6×100 ml)
  • dry with materialThe combined extracts were dried (K2CO3)
  • concentrationconcentrated
  • Sources & evidence

    ORD record
    ord-facf30b996f1484aaf341a84a6141e83
    Source dataset
    uspto-grants-2013_09
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US08524764B2

    Reaction notes

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