Hydrazine → HCID 58772592, compound

HRID 2250352Notes

Reaction equation

HRID 2250352 reaction equation
[NH2:1][NH2:2].[Cl:3][C:4]1[N:5]=[N:6][C:7](Cl)=[CH:8][C:9]=1[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1>N1C=CC=CC=1>[Cl:3][C:4]1[N:5]=[N:6][C:7]([NH:1][NH2:2])=[CH:8][C:9]=1[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 58772591HCID 58772591, compound

Product 1

HCID 58772592HCID 58772592, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

Anhydrous hydrazine (8 mL) was added to a solution of 3,6-dichloro-4-(4-chlorophenyl)pyridazine (7.1 g, 27.4 mmol) in pyridine (30 mL) at 100° C. The resulting mixture was stirred at 100° C. for 30 min. Analysis by HPLC/MS indicated the reaction was complete. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure to remove most of the pyridine. To the residue was added isopropanol (200 mL), the resulting suspension was refluxed for 20 min. After cooling to room temperature, the suspension was filtered. The collected solid was washed with isopropanol, dried in a 50° C. vacuum oven overnight to afford 4.0 g (57%) of the title compound as an off-white solid. LC/MS (method A): retention time=2.24 min, (M+H)+=255.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customto remove most of the pyridine
  4. additionTo the residue was added isopropanol (200 mL)
  5. temperaturethe resulting suspension was refluxed for 20 min
  6. temperatureAfter cooling to room temperature
  7. filtrationthe suspension was filtered
  8. washThe collected solid was washed with isopropanol
  9. customdried in a 50° C. vacuum oven overnight

Sources & evidence

ORD record
ord-2920fb589f9441aca1570fa6d3f0c11a
Source dataset
uspto-grants-2008_01
Patent number
US07317012B2

Reaction notes

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