Sodium Iodide → 3-Iodo[1,4]benzodioxino[2,3-c]pyridazine

HRID 1503210Notes

Reaction equation

HRID 1503210 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]2[O:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[O:11][C:4]=2[CH:3]=1.[I-:16].[Na+].I>C(OCC)(=O)C.C(=O)([O-])O.[Na+]>[I:16][C:2]1[N:7]=[N:6][C:5]2[O:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[O:11][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 24841Hydrogen iodideHCID 122134663-Chlorobenzo[5,6][1,4]dioxino[2,3-c]pyridazine

Product 1

HCID 895846403-Iodo[1,4]benzodioxino[2,3-c]pyridazineYield 27.6%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
140 °C

Procedure

Under an argon atmosphere, 3-chloro[1,4]benzodioxino[2,3-c]pyridazine (5.0 g), sodium iodide (6.79 g) and hydrogen iodide (55%) (57.98 g) were added and the mixture was stirred at 140° C. for 1 hr. The reaction mixture was diluted with ethyl acetate and aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted. The organic layer was dried over anhydrous sodium sulfate, and the solvent was concentrated under reduced pressure to give 3-iodo[1,4]benzodioxino[2,3-c]pyridazine (1.95 g).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationthe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-aaa65a21822d49259296ebf3080a7d51
Source dataset
uspto-grants-2015_12
Patent number
US09212147B2

Reaction notes

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