Ammonia → 6-Chloro-5-phenylpyridazin-3-amine

HRID 876865Notes

Reaction equation

HRID 876865 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[NH3:15]>>[Cl:1][C:2]1[N:3]=[N:4][C:5]([NH2:15])=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 113220803,6-Dichloro-4-phenylpyridazine

Product 1

HCID 569536546-Chloro-5-phenylpyridazin-3-amine

Conditions

Temperature
100 °C

Procedure

36.5 g (162 mmol) 3,6-Dichloro-4-phenyl-pyridazine were suspended in 1000 mL aqueous ammonia solution (25%) and stirred in an autoclave for 18 hours at 100° C. The reaction mixture was transferred into a separating funnel and the phases were separated. The aqueous phase was washed twice with dichloromethane. The combined organic phases were washed twice with water, the solvent was evaporated and the crude residue (two regioisomers, 6-chloro-5-phenyl-pyridazin-3-yl-amine and 6-chloro-4-phenyl-pyridazin-3-yl-amine 20.2 g=60.6%) was used without further purification in the next step.

Workup

  1. customThe reaction mixture was transferred into a separating funnel
  2. customthe phases were separated
  3. washThe aqueous phase was washed twice with dichloromethane
  4. washThe combined organic phases were washed twice with water
  5. customthe solvent was evaporated
  6. customthe crude residue (two regioisomers, 6-chloro-5-phenyl-pyridazin-3-yl-amine and 6-chloro-4-phenyl-pyridazin-3-yl-amine 20.2 g=60.6%) was used without further purification in the next step

Sources & evidence

ORD record
ord-d86b691a7b3748038c23de43af42d706
Source dataset
uspto-grants-2015_03
Patent number
US08987273B2

Reaction notes

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