Potassium Iodide → 3-[(2-Naphthyloxy)methyl][1,4]benzodioxino[2,3-c]pyridazine

HRID 1503211Notes

Reaction equation

HRID 1503211 reaction equation
Br[CH2:2][C:3]1[N:8]=[N:7][C:6]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[O:12][C:5]=2[CH:4]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+].[CH:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][C:26]=1[OH:35]>O.CN(C)C=O>[CH:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][C:26]=1[O:35][CH2:2][C:3]1[N:8]=[N:7][C:6]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[O:12][C:5]=2[CH:4]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 86632-NaphtholHCID 11430Potassium CarbonateHCID 1176911713-(Bromomethyl)[1,4]benzodioxino[2,3-c]pyridazine

Product 1

HCID 895846453-[(2-Naphthyloxy)methyl][1,4]benzodioxino[2,3-c]pyridazineYield 65.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To 3-(bromomethyl)[1,4]benzodioxino[2,3-c]pyridazine (500 mg) were added dimethylformamide (10 ml), potassium iodide (30 mg), potassium carbonate (750 mg) and 2-naphthylalcohol (290 mg), and the mixture was stirred at room temperature for 24 hr. Water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with 1M aqueous sodium hydroxide solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure, and the residue was washed with diethyl ether and the resulting solid was filtered and dried under reduced pressure to give 3-[(2-naphthyloxy)methyl][1,4]benzodioxino[2,3-c]pyridazine (400 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with 1M aqueous sodium hydroxide solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThe solvent was concentrated under reduced pressure
  5. washthe residue was washed with diethyl ether
  6. filtrationthe resulting solid was filtered
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-e3dbc379b74e477098d14e3a13ff124f
Source dataset
uspto-grants-2015_12
Patent number
US09212147B2

Reaction notes

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