Hydrazine hydrate (1:1) → 3-chloro-4-cyclobutyl-6-hydrazinylPyridazine

HRID 1596202Notes

Reaction equation

HRID 1596202 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][C:7]=1[CH:8]1[CH2:11][CH2:10][CH2:9]1.O.[NH2:14][NH2:15]>O1CCOCC1>[Cl:1][C:2]1[N:3]=[N:4][C:5]([NH:14][NH2:15])=[CH:6][C:7]=1[CH:8]1[CH2:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 219732193,6-Dichloro-4-cyclobutylpyridazine

Product 1

HCID 226099463-chloro-4-cyclobutyl-6-hydrazinylPyridazine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3,6-Dichloro-4-cyclobutylpyridazine (22.5 g, 0.11 mol) and hydrazine hydrate (34 ml, 0.66 mol) were heated at reflux in dioxan (280 ml) for 24 h. Upon cooling the desired isomer crystallized from the reaction and was collected by filtration (13.28 g, 64%). 1H NMR (250 MHz, d6-DMSO) 1.68-1.86 (1H, m), 2.00-2.11 (3H, m), 2.29-2.38 (2H, m), 3.52-3.61 (1H, m), 4.35 (2H, br), 6.99 (1H, s), 8.06 (1H, br); MS (ES+) m/e 198 [MH]+, 200 [MH]+.

Workup

  1. temperatureUpon cooling the desired isomer
  2. customcrystallized from the reaction
  3. filtrationwas collected by filtration (13.28 g, 64%)

Sources & evidence

ORD record
ord-228bce0a4cbe4403ab04d596598b7d46
Source dataset
uspto-grants-2001_09
Patent number
US06291460B1

Reaction notes

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