Hydrochloric Acid → 1-(2-(4-Methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one oxime

HRID 731702Notes

Reaction equation

HRID 731702 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]([C:18](=O)[CH:19]([CH3:21])[CH3:20])=[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][N:11]3[N:10]=2)=[CH:5][CH:4]=1.Cl.[NH2:24][OH:25].[OH-].[Na+].Cl>CCO.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]([C:18](=[N:24][OH:25])[CH:19]([CH3:21])[CH3:20])=[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][N:11]3[N:10]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 578375001-(2-(4-Methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one

Product 1

HCID 578374551-(2-(4-Methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one oximeYield 50.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 4.4 (14.9 mmol) of 1-(2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one in 32 ml of anhydrous EtOH was added 4.15 g of hydroxylamine hydrochloride, followed by a solution of 13.73 g (14.9 mmol) of NaOH in 10 ml water dropwise. The mixture was stirred and refluxed over night. After cooling, the solution was 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 g of crude product was obtained. Purification on an aluminum oxide column with hexane-dichloromethane-ethyl acetate as eluant afforded 2.33 g (50.5%) of 1-(2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one oxime. Compound 1022.

Workup

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

Sources & evidence

ORD record
ord-b48fa58bcfd04c79918e8e8b2725ce9b
Source dataset
uspto-grants-2009_09
Patent number
US07585875B2

Reaction notes

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