Acetone, oxime → HCID 13732595, compound

HRID 1731533Notes

Reaction equation

HRID 1731533 reaction equation
[CH3:1][C:2](=[N:4][OH:5])[CH3:3].CC(C)([O-])C.[K+].[C:12]([C:20]1[C:21](Cl)=[C:22]2[CH:28]=[N:27][N:26]([CH2:29][CH3:30])[C:23]2=[N:24][CH:25]=1)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O1CCCC1>[C:12]([C:20]1[C:21]([O:5][N:4]=[C:2]([CH3:3])[CH3:1])=[C:22]2[CH:28]=[N:27][N:26]([CH2:29][CH3:30])[C:23]2=[N:24][CH:25]=1)(=[O:19])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 67180Acetone, oximeHCID 12281138HCID 12281138, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 13732595HCID 13732595, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 25 ml of dry tetrahydrofuran (THF hereafter) was dissolved 1.6 g of acetone oxime, followed by 2.46 g of potassium t-butoxide. After stirring 0.5 hour 5.0 g of 5-benzoyl-4-chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine in 50 ml of THF was added to the solution. After an additional 0.5 hour the reaction was quenched with ammonium chloride solution and the product was extracted with ether. Evaporation of the organic phase and recrystallization of the residue from ethanol gave 4.1 g of product, mp 115°-116° C.

Workup

  1. additionwas added to the solution
  2. customAfter an additional 0.5 hour the reaction was quenched with ammonium chloride solution
  3. extractionthe product was extracted with ether
  4. customEvaporation of the organic phase and recrystallization of the residue from ethanol

Sources & evidence

ORD record
ord-e9fb46420b40460aa15eeb44bd1e4873
Source dataset
uspto-grants-1986_11
Patent number
US04622326

Reaction notes

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