Hydrazine hydrate (1:1) → [6-chloro-5-(3,6-dihydro-2H-pyridin-1-yl)-pyridazin-3-yl]hydrazine

HRID 429743Notes

Reaction equation

HRID 429743 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][C:7]=1[N:8]1[CH2:13][CH:12]=[CH:11][CH2:10][CH2:9]1.O.[NH2:16][NH2:17]>O1CCOCC1>[Cl:1][C:2]1[N:3]=[N:4][C:5]([NH:16][NH2:17])=[CH:6][C:7]=1[N:8]1[CH2:13][CH:12]=[CH:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 183533373,6-dichloro-4-(3,6-dihydro-2H-pyridin-1-yl)pyridazine

Product 1

HCID 18353340[6-chloro-5-(3,6-dihydro-2H-pyridin-1-yl)-pyridazin-3-yl]hydrazineYield 88%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A mixture of 3,6-dichloro-4-(3,6-dihydro-2H-pyridin-1-yl)pyridazine (1.7 g, 7.4 mmol) and hydrazine hydrate (2.2 ml) in dioxan was stirred and heated at reflux under nitrogen for 24 hours. Upon cooling the dioxan was removed in vacuo and the residue was partitioned between dichloromethane and water. The aqueous was further extracted with dichloromethane (×3). The combined extracts were dried (MgSO4), filtered and evaporated. The residue was triturated with ether/MeOH and dried in vacuo to afford the title pyridazine (1.5 g, 88%). 1H NMR (250 MHz, d6-DMSO) 7.8 (1H, br s), 6.48 (1H, s), 5.76 (2H, m), 4.21 (2H, br s), 3.51 (2H, m), 3.24 (2H, m), 2.16 (2H, m). MS (ES+) 226 [MH]+, 228 [MH]+.

Workup

  1. temperatureheated
  2. temperatureat reflux under nitrogen for 24 hours
  3. customwas removed in vacuo
  4. customthe residue was partitioned between dichloromethane and water
  5. extractionThe aqueous was further extracted with dichloromethane (×3)
  6. dry with materialThe combined extracts were dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was triturated with ether/MeOH
  10. customdried in vacuo

Sources & evidence

ORD record
ord-6aa1386310a7485b993da535d56de599
Source dataset
uspto-grants-2001_11
Patent number
US06319924B1

Reaction notes

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