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

HRID 2224254Notes

Reaction equation

Cl[C:2]1[N:3]=[N:4][CH:5]=[C:6]([Cl:15])[C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1.[NH2:16][NH2:17]>O1CCOCC1>[Cl:15][C:6]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)=[C:2]([NH:16][NH2:17])[N:3]=[N:4][CH:5]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 3,5-dichloro-4-(4-chlorophenyl)pyridazine (2.56 g, 10 mmol) in dioxane (36 mL) at RT was added hydrazine (3.2 mL, 100 mL). After addition, the reaction was heated to 70° C. for 2 h. After cooling to RT, the reaction was concentrated under reduced pressure. To the obtained residue was added 2-propanol (80 mL) and the resulting white solid was removed by filtration. The collected liquid was concentrated under reduced pressure to give the title compound 1-(5-chloro-4-(4-chlorophenyl)pyridazin-3-yl)hydrazine as an off-white solid (560 mg, 22%) which contained 15% of by-product (1-(3-chloro-4-(4-chlorophenyl)pyridazin-5-yl)hydrazine). The mixture was used directly in the next step, 273E. LC/MS (method A): RT=1.89 min, (M+H)+=255.

Workup

additionAfter addition
temperatureAfter cooling to RT
concentrationthe reaction was concentrated under reduced pressure
additionTo the obtained residue was added 2-propanol (80 mL)
customthe resulting white solid was removed by filtration
concentrationThe collected liquid was concentrated under reduced pressure

Sources & evidence

ORD record: ord-860a3efc2cec4c0fab1cf25e9452efd2
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07378418B2

Reaction notes

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