Hydrazine hydrate (1:1) → 1-(5-(4-Chlorophenyl)-4-(pyridin-4-yl)pyridazin-3-yl)hydrazine

HRID 2224240Notes

Reaction equation

HRID 2224240 reaction equation
Cl[C:2]1[N:3]=[N:4][CH:5]=[C:6]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[C:7]=1[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1.O.[NH2:22][NH2:23]>N1C=CC=CC=1>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([C:6]2[C:7]([C:8]3[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=3)=[C:2]([NH:22][NH2:23])[N:3]=[N:4][CH:5]=2)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 597168553-Chloro-5-(4-chlorophenyl)-4-(pyridin-4-yl)pyridazine

Product 1

HCID 597169001-(5-(4-Chlorophenyl)-4-(pyridin-4-yl)pyridazin-3-yl)hydrazineYield 88%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Chloro-5-(4-chlorophenyl)-4-(pyridin-4-yl)pyridazine (5.1 g, 16.9 mmol) was dissolved in pyridine (20 mL) and hydrazine mono-hydrate (17.0 mL, 350.5 mmol) was added. The reaction mixture was stirred at reflux for 40 min. After this time, the reaction mixture was cooled to RT and then concentrated to half of the original volume under reduced pressure. The resultant mixture was diluted with water (100 mL). The yellow colored solid was collected by filtration and rinsed thoroughly with water. The solid was dried in a vacuum oven at 40° C. to give the title compound, 1-(5-(4-chlorophenyl)-4-(pyridin-4-yl)pyridazin-3-yl)hydrazine, (4.4 g, 88%) as a yellow powder. HPLC: 1.01 min; MS, M+H=298.

Workup

  1. temperatureat reflux for 40 min
  2. concentrationconcentrated to half of the original volume under reduced pressure
  3. additionThe resultant mixture was diluted with water (100 mL)
  4. filtrationThe yellow colored solid was collected by filtration
  5. washrinsed thoroughly with water
  6. customThe solid was dried in a vacuum oven at 40° C.

Sources & evidence

ORD record
ord-eae5acadcf7240168fda17e5d2102827
Source dataset
uspto-grants-2008_05
Patent number
US07378418B2

Reaction notes

Loading…