Sodium Hydroxide → 1-(2-(4-Chlorophenyl)pyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one oxime

HRID 731705Notes

Reaction equation

HRID 731705 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]([C:17](=O)[CH:18]([CH3:20])[CH3:19])=[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.Cl.[NH2:23][OH:24].[OH-].[Na+]>CCO.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]([C:17](=[N:23][OH:24])[CH:18]([CH3:20])[CH3:19])=[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 578374761-(2-(4-Chlorophenyl)pyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one

Product 1

HCID 578374911-(2-(4-Chlorophenyl)pyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one oximeYield 50.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3.5 g (11.7 mmol) of 1-(2-(4-chlorophenyl)pyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one in 65 ml of anhydrous EtOH was added 3.25 g of hydroxylamine hydrochloride, followed by a solution of 2.92 g (11.7 mmol) NaOH in 8 ml water dropwise. The mixture was stirred and refluxed over night. After cooling, the solution was evaporated and poured into a solution of 6 ml 6N HCl and 100 ml ice water with stirring for 30 minutes. The mixture was extracted with ethyl acetate three times. The organic phase was washed with brine and dried over MgSO4. After evaporation of the solvent under vacuum, 5.11 g of crude product was obtained. Purification on an aluminum oxide column with hexane-dichloromethane-ethyl acetate as eluant furnished 1.86 g (50.7%) of 1-(2-(4-chlorophenyl)pyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one oxime. Compound 1025.

Workup

  1. temperaturerefluxed over night
  2. temperatureAfter cooling
  3. customthe solution was evaporated
  4. additionpoured into a solution of 6 ml 6N HCl and 100 ml ice water
  5. stirringwith stirring for 30 minutes
  6. extractionThe mixture was extracted with ethyl acetate three times
  7. washThe organic phase was washed with brine
  8. dry with materialdried over MgSO4
  9. customAfter evaporation of the solvent under vacuum
  10. custom5.11 g of crude product was obtained
  11. customPurification on an aluminum oxide column with hexane-dichloromethane-ethyl acetate as eluant

Sources & evidence

ORD record
ord-328fe56bcb2945f786f1aeec814e8be1
Source dataset
uspto-grants-2009_09
Patent number
US07585875B2

Reaction notes

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