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

HRID 380322

Reaction equation

HRID 380322 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 dioxane (280 ml) for 24 hours. Upon cooling the desired isomer crystallized from the reaction and was collected by filtration (13.3 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 (13.3 g, 64%)

Sources & evidence

ORD record
ord-ee749b0974f94195a9d027d4446f3588
Source dataset
uspto-grants-2001_10
Patent number
US06303605B1

Linked notes

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