Hydrazine → HCID 86599008, compound

HRID 2224283Notes

Reaction equation

HRID 2224283 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][CH:5]=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[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]([CH3:15])=[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]([CH3:15])=[CH:11][CH:10]=2)[C:7]=1[NH:16][NH2:17]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 59716905HCID 59716905, compound

Product 2

HCID 59716608HCID 59716608, compoundHCID 86599008HCID 86599008, compoundYield 162.3%

Conditions

Temperature
60 °C

Procedure

To a stirring suspension of 3,4-dichloro-5-p-tolylpyridazine (4.5 g, 18.9 mmol) in 2-BuOH (200 mL) at room temperature was added anhydrous hydrazine (9.1 g, 284 mmol). The reaction mixture was heated at 60° C. under argon. HPLC/MS analysis indicated complete reaction after 15 h. The reaction mixture was cooled to 0° C., and the product was collected by filtration and further washed with ice-cold 2-propanol (20 mL×2). After drying under vacuum at room temperature for 16 h, the title compound, 1-(4-chloro-5-p-tolylpyridazin-3-yl)hydrazine, was obtained in a 2.6:1 ratio with undesired 1-(3-chloro-5-p-tolylpyridazin-4-yl)hydrazine (3.6 g gross). 1-(4-chloro-5-p-tolylpyridazin-3-yl)hydrazine MS [M+H]+ 235; HPLC retention time=1.84 min. 1-(3-chloro-5-p-tolylpyridazin-4-yl)hydrazine MS [M+H]+ 235; HPLC retention time=1.35 min.

Workup

  1. customreaction after 15 h
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. filtrationthe product was collected by filtration
  4. washfurther washed with ice-cold 2-propanol (20 mL×2)
  5. customAfter drying under vacuum at room temperature for 16 h

Sources & evidence

ORD record
ord-b74617ee1a344f6a9af8af1700289d8f
Source dataset
uspto-grants-2008_05
Patent number
US07378418B2

Reaction notes

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