Lithium hydride → 3-Chloro-6,7-dihydro-[1,4]dioxino[2,3-c]pyridazine

HRID 15170

Reaction equation

HRID 15170 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([Cl:12])=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][OH:11].[H-].[Li+]>O1CCOCC1>[Cl:12][C:5]1[N:4]=[N:3][C:2]2[O:11][CH2:10][CH2:9][O:8][C:7]=2[CH:6]=1

Participants

4

Reactant 2

HCID 62714Lithium hydrideHCID 817635472-[(3,6-Dichloro-4-pyridazinyl)oxy]ethanol

Product 1

HCID 552674403-Chloro-6,7-dihydro-[1,4]dioxino[2,3-c]pyridazine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-[(3,6-dichloro-4-pyridazinyl)oxy]ethanol containing some bromo-derivative (15.46 g; 0.0703 mol) in dry 1,4-dioxane (1.2 L) was treated with lithium hydride (2.3 g; 0.28 mol) in portions and stirred at room temperature for 1 hour under argon, then heated at 110° C. overnight. The reaction mixture was quenched with wet 1,4-dioxane, then iced-water. The solution was evaporated to half volume, taken to pH 8 with 5M hydrochloric acid and evaporated to dryness. Water was added and the residue was extracted 5× with chloroform, dried (sodium sulphate) and evaporated to afford a white solid (12.4 g, ca. 77%) (containing ca. 15% of a bromo species).

Workup

  1. temperatureheated at 110° C. overnight
  2. customThe reaction mixture was quenched with wet 1,4-dioxane
  3. customThe solution was evaporated to half volume
  4. customevaporated to dryness
  5. additionWater was added
  6. extractionthe residue was extracted 5× with chloroform
  7. dry with materialdried (sodium sulphate)
  8. customevaporated
  9. customto afford

Sources & evidence

ORD record
ord-ce358187d37146d6ae74d6a3c5e65e0d
Source dataset
uspto-grants-2010_06
Patent number
US07732460B2

Linked notes

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