Isopropyl nitrite → 1-Phenyl-3,5-dimethyl-4-(2'-oximino acetyl)-pyrazole

HRID 1447298Notes

Reaction equation

HRID 1447298 reaction equation
[C:1]1([N:7]2[C:11]([CH3:12])=[C:10]([C:13](=[O:15])[CH3:14])[C:9]([CH3:16])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:17](OC(C)C)=[O:18].[Na]>C(O)C>[C:1]1([N:7]2[C:11]([CH3:12])=[C:10]([C:13](=[O:15])[CH:14]=[N:17][OH:18])[C:9]([CH3:16])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 10929Isopropyl nitriteHCID 6079231-(3,5-Dimethyl-1-phenyl-1H-pyrazol-4-yl)ethanoneHCID 5360545Sodium

Product 1

HCID 572593731-Phenyl-3,5-dimethyl-4-(2'-oximino acetyl)-pyrazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
7 °C

Procedure

1-Phenyl-3,5-dimethyl-4-acetyl pyrazole (Chem. Abs. 63, 16332) (53 g) was dissolved in absolute ethanol (120 ml) and cooled to 7° C. Isopropyl nitrite (29.3 g) was added followed by a solution of sodium (5.7 g) in absolute ethanol (110 ml). The mixture was stirred 18 hours at 0°-10° C. and the fawn coloured sodium salt of the oxime filtered and washed with acetone (25 ml). The filter cake was then dissolved in water (40 ml) and the solution acidified with acetic acid (7 ml). The mixture was then extracted with chloroform (200 ml) and the chloroform extract dried over anhydrous sodium sulphate and then concentrated under vacuum to give 1-phenyl-3,5-dimethyl-4-(2'-oximino acetyl)-pyrazole as a yellow coloured solid.

Workup

  1. filtrationthe fawn coloured sodium salt of the oxime filtered
  2. washwashed with acetone (25 ml)
  3. dissolutionThe filter cake was then dissolved in water (40 ml)
  4. extractionThe mixture was then extracted with chloroform (200 ml)
  5. extractionthe chloroform extract
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9fe9243a852541f0b48e9f3fcc991a18
Source dataset
uspto-grants-1982_02
Patent number
US04316815

Reaction notes

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