Hydrazine hydrate (1:1) → 3-Chloro-6-hydrazinyl-4-(1-pyrrolidinyl)pyridazine

HRID 380326Notes

Reaction equation

HRID 380326 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][C:7]=1[N:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1.O.[NH2:15][NH2:16]>O1CCOCC1>[Cl:1][C:2]1[N:3]=[N:4][C:5]([NH:15][NH2:16])=[CH:6][C:7]=1[N:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 124492983,6-Dichloro-4-pyrrolidin-1-ylpyridazine

Product 1

HCID 226099553-Chloro-6-hydrazinyl-4-(1-pyrrolidinyl)pyridazine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3,6-Dichloro-4-(pyrrolidin-1-yl)pyridazine (7.2 g, 33 mmol) and hydrazine hydrate (9.96 g, 0.2 mol) were heated at reflux in dioxan (130 ml) for 6 hours. Upon cooling the desired isomer crystallized from the reaction and was collected by filtration (4.1 g, 58%). 1H NMR (250 MHz , d6-DMSO) 1.79-1.84 (4H, m), 3.25-3.40 (4H, m), 4.12 (2H, br), 6.09 (1H, s), 7.47 (1H, s). MS (ES+) 214 [MH]+, 216 [MH]+.

Workup

  1. temperatureUpon cooling the desired isomer
  2. customcrystallized from the reaction
  3. filtrationwas collected by filtration (4.1 g, 58%)

Sources & evidence

ORD record
ord-358a358317e3498c9a8490709cd30ddc
Source dataset
uspto-grants-2001_10
Patent number
US06303605B1

Reaction notes

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