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

HRID 2224269Notes

Reaction equation

HRID 2224269 reaction equation
Cl[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].O.[NH2:17][NH2:18]>C(O)C(C)C>[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:17][NH2:18]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 597167833,4-Dichloro-5-(4-chlorophenyl)pyridazine

Product 1

HCID 597166211-(4-Chloro-5-(4-chlorophenyl)pyridazin-3-yl)hydrazineYield 84.8%

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent

Procedure

3,4-Dichloro-5-(4-chlorophenyl)-pyridazine (6.0 g, 23.1 mmol) was suspended in isobutanol (150 mL) at 0° C. and hydrazine monohydrate (11.1 g) was added dropwise over 10 min. The reaction mixture was slowly warmed up to RT and stirred for 24 h. The mixture was cooled in an ice/water bath for 15 min and filtered. The white solid thus obtained was washed with cold isopropanol and dried to give the title compound, 1-[4-chloro-5-(4-chloro-phenyl)-pyridazin-3-yl]-hydrazine, (5.0 g) as a white solid. HPLC: 1.65 min.

Workup

  1. temperatureThe mixture was cooled in an ice/water bath for 15 min
  2. filtrationfiltered
  3. customThe white solid thus obtained
  4. washwas washed with cold isopropanol
  5. customdried

Sources & evidence

ORD record
ord-f6cabf6ac60a40e4826f26742691130c
Source dataset
uspto-grants-2008_05
Patent number
US07378418B2

Reaction notes

Loading…