Potassium Hydroxide → HCID 59437142, compound

HRID 2089572Notes

Reaction equation

HRID 2089572 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

Conditions

Temperature
0 °C

Procedure

3-Iodo-7-nitro-1H-indazole (2.50 g, 8.65 mmol) prepared in Step A was dissolved in acetone (50 mL). Potassium hydroxide (0.73 g, 12.97 mmol) and 4-methoxybenzylchloride (1.63 g, 10.38 mmol) were added in drops thereto at 0° C., and the mixture was stirred for 2 h. After completion of the reaction, the reaction mixture was diluted with water, extracted with ethyl acetate, washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under reduced pressure, and the residue was purified by column chromatography to give the title compound (3.2 g, Yield 91%).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. washwashed with saturated aqueous 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 purified by column chromatography

Sources & evidence

ORD record
ord-7cb627285e704b7ba068b5d6bc5bbcac
Source dataset
uspto-grants-2013_05
Patent number
US08436038B2

Reaction notes

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