Catechol → 3-Chlorobenzo[5,6][1,4]dioxino[2,3-c]pyridazine

HRID 1821661Notes

Reaction equation

HRID 1821661 reaction equation
[H-].[Na+].[C:3]1([C:5](=[CH:7][CH:8]=[CH:9][CH:10]=1)[OH:6])[OH:4].[Cl:11][C:12]1[N:13]=[N:14][C:15](Cl)=[CH:16][C:17]=1Cl>O1CCOCC1>[Cl:11][C:12]1[N:13]=[N:14][C:15]2[O:4][C:3]3[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=3[O:6][C:16]=2[CH:17]=1

Participants

5

Reactant 3

HCID 289CatecholHCID 24758Sodium hydrideHCID 951233,4,6-Trichloropyridazine

Product 1

HCID 122134663-Chlorobenzo[5,6][1,4]dioxino[2,3-c]pyridazineYield 69.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent3×

Procedure

In 1,4-dioxane (30 mL) was suspended 3.49 g (80.0 mmol) of 55% sodium hydride, and to the suspension were added a 1,4-dioxane (30 mL) solution containing 4.40 g (40 mmol) of pyrocatechol, then a 1,4-dioxane (30 mL) solution containing 7.30 g (39.9 mmol) of 3,4,6-trichloropyridazine {described in The Journal of Organic Chemistry, 1963, vol. 28, pp. 218 to 221}, and the mixture was refluxed for 2 hours. The reaction mixture was poured into ice-cold water, and extracted with ethyl acetate. The organic layers were combined, washed successively with 1 mol/L sodium hydroxide and water, and dried over anhydrous magnesium sulfate. The solvent was removed, and the residue was recrystallized from methyl isobutyl ketone to obtain 6.15 g (27.8 mmol, Yield: 69.7%) of 3-chloro[1,4]benzodioxino[2,3-c]pyridazine.

Workup

  1. temperature218 to 221}, and the mixture was refluxed for 2 hours
  2. additionThe reaction mixture was poured into ice-cold water
  3. extractionextracted with ethyl acetate
  4. washwashed successively with 1 mol/L sodium hydroxide and water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed
  7. customthe residue was recrystallized from methyl isobutyl ketone

Sources & evidence

ORD record
ord-40b490f9e4d34c3aa0d317a012f415d6
Source dataset
uspto-grants-2009_10
Patent number
US07608563B2

Reaction notes

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