Potassium Hydroxide → HCID 70817365, compound

HRID 82217Notes

Reaction equation

HRID 82217 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8]([CH2:14][C:15]([O:17]CC)=[O:16])=[N:9][N:10]2[CH3:13])=[CH:6][CH:5]=1>CO>[Cl:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8]([CH2:14][C:15]([OH:17])=[O:16])=[N:9][N:10]2[CH3:13])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 70847731Ethyl (6-chloro-1-methyl-1H-indazol-3-yl)acetate

Product 1

HCID 70817365HCID 70817365, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

Aqueous potassium hydroxide (5.93 mL, 10%) was added to ethyl (6-chloro-1-methyl-1H-indazol-3-yl)acetate (Preparation 169, 1.78 g, 0.704 mol) in MeOH (30 mL). The mixture was stirred for 1 hour at 25° C. then the methanol was evaporated in vacuo. The aqueous residue was washed with diethyl ether (30 mL) then acidified with aqueous HCl (6 M). The mixture was extracted with ethyl acetate (30 mL) and the organic phase was dried over sodium sulphate, evaporated in vacuo and purified by column chromatography on silica gel (DCM:MeOH 95:5) to afford the title compound as a white solid in 56% yield, 865 mg.

Workup

  1. customthe methanol was evaporated in vacuo
  2. washThe aqueous residue was washed with diethyl ether (30 mL)
  3. extractionThe mixture was extracted with ethyl acetate (30 mL)
  4. dry with materialthe organic phase was dried over sodium sulphate
  5. customevaporated in vacuo
  6. custompurified by column chromatography on silica gel (DCM:MeOH 95:5)

Sources & evidence

ORD record
ord-26182695954a45acb00e1e49a0ed6aaf
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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