Potassium Hydroxide → HCID 59437142, compound

HRID 1802829Notes

Reaction equation

HRID 1802829 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[C:6]([N+:11]([O-:13])=[O:12])[CH:7]=[CH:8][CH:9]=2)[NH:4][N:3]=1.[OH-].[K+].[CH3:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Cl)=[CH:20][CH:19]=1>CC(C)=O.O>[I:1][C:2]1[C:10]2[C:5](=[C:6]([N+:11]([O-:13])=[O:12])[CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:22][C:21]2[CH:24]=[CH:25][C:18]([O:17][CH3:16])=[CH:19][CH:20]=2)[N:3]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 699934-Methyloxybenzyl chlorideHCID 178526522HCID 178526522, compound

Product 1

HCID 59437142HCID 59437142, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

3-Iodo-7-nitro-1H-indazole (2.50 g, 8.65 mmol) obtained in Step 1 was dissolved in acetone (50 mL), and thereto potassium hydroxide (0.73 g, 12.97 mmol) and 4-methoxybenzylchloride (1.63 g, 10.38 mmol) were added in drops at 0° C. The mixture was stirred for 2 hours. At the end of reaction, the mixture was diluted with water, and extracted with ethylacetate. The extract was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and filtered. The solvent was removed under reduced pressure and the residue was separated by column chromatography to give 3-iodo-7-nitro-1-(4-methoxybenzyl)-1H-indazole (3.2 g, Yield 91%).

Workup

  1. customAt the end of reaction
  2. extractionextracted with ethylacetate
  3. washThe extract was washed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was separated by column chromatography

Sources & evidence

ORD record
ord-c5c2f5c1439545fc82a16c6e845195d1
Source dataset
uspto-grants-2013_01
Patent number
US08349885B2

Reaction notes

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