Potassium Hydroxide → HCID 59437142, compound

HRID 1466484Notes

Reaction equation

HRID 1466484 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-1060bebe49a34d2fb6306cb850e1fec2
Source dataset
uspto-grants-2015_04
Patent number
US09000028B2

Reaction notes

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