Potassium Cyanide → 3-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-3-oxopropanenitrile

HRID 38233Notes

Reaction equation

HRID 38233 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13](=[O:16])[CH2:14]Br)[CH:10]=[N:9]2)=[CH:5][CH:4]=1.[C-:19]#[N:20].[K+]>O.CO.C1COCC1.O>[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13](=[O:16])[CH2:14][C:19]#[N:20])[CH:10]=[N:9]2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 866423312-Bromo-1-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)ethanone

Product 1

HCID 666687013-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-3-oxopropanenitrileYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

According to Scheme 5 Step 1: A solution of 1-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-2-bromoethanone (9.70 mmol, 3.00 g) and potassium cyanide (14.6 mmol, 948 mg) in 120 mL of water/MeOH/THF (1:1:1) was stirred for 30 minutes at room temperature. The reaction mixture was diluted with water (150 mL) and the aqueous phase was extracted with DCM. The organic phase was dried over MgSO4, was filtered and was concentrated to yield 3-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-3-oxopropanenitrile (9.40 mmol, 2.40 g, 97%).

Workup

  1. extractionthe aqueous phase was extracted with DCM
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationwas filtered
  4. concentrationwas concentrated

Sources & evidence

ORD record
ord-8e63536ced844186a69e55057e64ea4f
Source dataset
uspto-grants-2013_09
Patent number
US08524718B2

Reaction notes

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