Dichloromethane → 3-Chloro-6-hydrazinyl-4-(1-pyrrolidinyl)pyridazine

HRID 47227Notes

Reaction equation

HRID 47227 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].ClCCl>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

5

Reactant 3

HCID 6344DichloromethaneHCID 24654Hydrazine hydrate (1:1)HCID 124492983,6-Dichloro-4-pyrrolidin-1-ylpyridazine

Product 1

HCID 226099553-Chloro-6-hydrazinyl-4-(1-pyrrolidinyl)pyridazineYield 27.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 3,6-dichloro-4-(pyrrolidin-1-yl)pyridazine (53 g, 0.24 mol) and hydrazine monohydrate (105 ml, 2.2 mol) in 1,4-dioxane (820 ml) was heated at reflux overnight. The solution was allowed to cool, and dichloromethane was added, precipitating a solid. This was filtered off, affording the title compound as a pale yellow solid (14 g, 27%). The filtrate was concentrated in vacuo, and the residue purified by flash chromatography on silica gel, eluting with 2-5% methanol in dichloromethane containing 0.1% concentrated aqueous ammonia, yielding a further 5 g (4%) of the title compound. 1H NMR (250 MHz, CDCl3) δ1.98 (4H, m), 3.26 (2H, br s), 3.57 (4H, m), 6.11 (1H, s), 6.41 (1H, br s). MS (ES+) m/e 214 [MH]+, 216 [MH]+.

Workup

  1. temperatureat reflux overnight
  2. temperatureto cool
  3. customprecipitating a solid
  4. filtrationThis was filtered off

Sources & evidence

ORD record
ord-675d41ed74c142818d21dedd4c944bbd
Source dataset
uspto-grants-2004_03
Patent number
US06699859B1

Reaction notes

Loading…