Hydrazine hydrate (1:1) → HCID 90411376, compound

HRID 1850686Notes

Reaction equation

HRID 1850686 reaction equation
Cl[C:2]1[N:3]=[N:4][CH:5]=[C:6]([N:9]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]2)[C:7]=1[Cl:8].O.[NH2:17][NH2:18]>CCOCC>[Cl:8][C:7]1[C:6]([N:9]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]2)=[CH:5][N:4]=[N:3][C:2]=1[NH:17][NH2:18]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 90411760HCID 90411760, compound

Product 1

HCID 90411376HCID 90411376, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

3,4-Dichloro-5-(4-methylpiperazin-1-yl)pyridazine (500 mg, 2.023 mmol) was placed in a microwave tube and hydrazine monohydrate (1.772 g, 1.717 mL, 35.40 mmol) was added. The resulting suspension was stirred at 100° C. for ˜10 mins. The brown reaction mixture was allowed to cool to RT, whereupon solid started to precipitate. The suspension was sonicated and the suspended solid was collected by filtration. This material was dissolved in water, basified with saturated NaHCO3 and partitioned with 10% MeOH in DCM. The aqueous layer was extracted with further 10% MeOH in DCM (6×10 mL) and the combined organics were dried over Na2SO4, filtered and concentrated under reduced pressure to give a yellow solid. This material was sonicated in ether and the suspended solid was collected by filtration to give [4-chloro-5-(4-methylpiperazin-1-yl)pyridazin-3-yl]hydrazine as an ochre powder (155.9 mg, 32% Yield).

Workup

  1. temperatureto cool to RT, whereupon solid
  2. customto precipitate
  3. customThe suspension was sonicated
  4. filtrationthe suspended solid was collected by filtration
  5. dissolutionThis material was dissolved in water
  6. custompartitioned with 10% MeOH in DCM
  7. extractionThe aqueous layer was extracted with further 10% MeOH in DCM (6×10 mL)
  8. dry with materialthe combined organics were dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customto give a yellow solid
  12. filtrationthe suspended solid was collected by filtration

Sources & evidence

ORD record
ord-f63a130e94944e21915ae924fac0b46d
Source dataset
uspto-grants-2015_02
Patent number
US08957078B2

Reaction notes

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