Acetone, oxime → HCID 13732595, compound

HRID 542565Notes

Reaction equation

HRID 542565 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 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-f07f2c410c744692b362dfb018c5e4b9
Source dataset
uspto-grants-1987_04
Patent number
US04658029

Reaction notes

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