Hydrazine → 1-(3-Chloro-5-(4-chlorophenyl)pyridazin-4-yl)hydrazine

HRID 2224279Notes

Reaction equation

HRID 2224279 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][CH:5]=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[C:7]=1[Cl:8].[NH2:16][NH2:17]>>[Cl:8][C:7]1[C:6]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[CH:5][N:4]=[N:3][C:2]=1[NH:16][NH2:17].[Cl:1][C:2]1[N:3]=[N:4][CH:5]=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[C:7]=1[NH:16][NH2:17]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 597167833,4-Dichloro-5-(4-chlorophenyl)pyridazine

Product 2

HCID 597166211-(4-Chloro-5-(4-chlorophenyl)pyridazin-3-yl)hydrazineHCID 865990071-(3-Chloro-5-(4-chlorophenyl)pyridazin-4-yl)hydrazineYield 169.3%

Conditions

Temperature
60 °C

Procedure

To a stirring suspension of 3,4-dichloro-5-(4-chlorophenyl)pyridazine (2.58 g, 10 mmol) in 2-BuOH (150 mL) at RT was added anhydrous hydrazine (4.80 g, 150 mmol). The reaction mixture was heated at 60° C. under argon. HPLC/MS analysis indicated that the reaction was complete after 5 h. The reaction mixture was cooled to 0° C., and the product was collected by filtration. The solid was then washed with ice-cold 2-propanol (10 mL×2). After drying the solid under vacuum at room temperature for 16 h, the title compound, 1-(4-chloro-5-(4-chlorophenyl)pyridazin-3-yl)hydrazine was obtained in a 1.6:1 ratio with undesired 1-(3-chloro-5-(4-chlorophenyl)pyridazin-4-yl)hydrazine (2.16 g gross). 1-(4-chloro-5-(4-chlorophenyl)pyridazin-3-yl)hydrazine MS [M+H]+ 255; HPLC retention time=1.63 min. 1-(3-chloro-5-(4-chlorophenyl)pyridazin-4-yl)hydrazine MS [M+H]+ 255; HPLC retention time=1.09 min.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. filtrationthe product was collected by filtration
  3. washThe solid was then washed with ice-cold 2-propanol (10 mL×2)
  4. customAfter drying the solid under vacuum at room temperature for 16 h

Sources & evidence

ORD record
ord-c9a16076f996456e92c71df6e604bd9d
Source dataset
uspto-grants-2008_05
Patent number
US07378418B2

Reaction notes

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