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Chemical Structure| 54367-66-7 Chemical Structure| 54367-66-7

Structure of 54367-66-7

Chemical Structure| 54367-66-7

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Product Details of [ 54367-66-7 ]

CAS No. :54367-66-7
Formula : C5H5ClN2O2
M.W : 160.56
SMILES Code : O=C(C1=C(Cl)N(C)N=C1)O
MDL No. :MFCD02089694
InChI Key :SDYOVMHXYNKROV-UHFFFAOYSA-N
Pubchem ID :2735774

Safety of [ 54367-66-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 54367-66-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 54367-66-7 ]

[ 54367-66-7 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 54367-66-7 ]
  • [ 10234-66-9 ]
YieldReaction ConditionsOperation in experiment
92.3% In sodium hydroxide; EXAMPLE 1 Preparation of 1-methyl-2-pyrazolin-5-one In a 250 ml autoclave, 10 g (0.0623 mol) of 5-chloro-1-methyl-4-pyrazolecarboxylic acid were dissolved in 100 g of 25% by weight strength aqueous sodium hydroxide solution (=0.623 mol). The solution was heated at 175 C. for 6 h. During this time, the pressure increased to 6 bar. After cooling, the autoclave was vented to atmospheric pressure. The reaction mixture was then adjusted to pH 1.5 using 60% by weight strength sulfuric acid. This resulted in evolution of CO2. After several minutes, the pH was adjusted to 6.5 using 25% by weight strength aqueous sodium hydroxide solution, and the resulting solution was concentrated under reduced pressure to dryness. The solid residue was transferred into a Soxhlet apparatus and continuously extracted with ethanol. Distillative removal of the ethanol under reduced pressure gave 5.7 g of the target compound of a purity of 98.9% (determined by gas chromatography). The melting point was 113 C. This corresponds to a yield of 92.3% of theory. The product was identified by the mixed melting point with an authentic sample.
92.3% In sodium hydroxide; EXAMPLE 13 Preparation of 1-methyl-2-pyrazolin-5-one 10 g (0.0623 mol) of 5-chloro-1-methyl-4-pyrazolecarboxylic acid were dissolved in 100 g of 25% by weight sodium hydroxide solution (=0.623 mol) in a 250 ml autoclave. The solution was heated at 175 C. for 6 h. The pressure rose to 6 bar during this. Cooling was followed by decompression to atmospheric pressure. The reaction mixture was then adjusted to pH 1.5 with 60% by weight sulfuric acid. CO2 evolution occurred during this. After a few minutes, the pH was adjusted to 6.5 with 25% by weight sodium hydroxide solution, and the resulting solution was evaporated to dryness in vacuo. The solid residue was transferred into a 45 Soxhlet apparatus and extracted continuously with ethanol. Removal of the ethanol by distillation in vacuo resulted in 5.7 g of a target compound with a purity of 98.9% (determined by gas chromatography). The melting point was 113 C. This corresponds to a yield of 92.3% of theory. The product was identified through a mixed melting point with an authentic sample.
  • 2
  • [ 57707-21-8 ]
  • [ 54367-66-7 ]
  • [ 10234-66-9 ]
YieldReaction ConditionsOperation in experiment
92.5% With sodium hydroxide; EXAMPLE 15 Preparation of 1-methyl-2-pyrazolin-5-one, Workup by Liquid/Liquid Extraction 10 g of 5-chloro-1-methylpyrazole-4-carboxylic acid were reacted as in Example 1 initially with 100 g of 25% by weight sodium hydroxide solution and subsequently under acidic conditions. After the acidic reaction mixture had been neutralized to pH 6.5 with 25% by weight sodium hydroxide solution, the reaction mixture was transferred into a liquid/liquid extractor and extracted with isobutanol at the boiling point of the solvent. After isolation of the organic phase and removal of the isobutanol by distillation, 5.8 g of 1-methyl-2-pyrazolinone remained (GC purity: 98.1%). The melting point was 112 C. The yield was 92.5% of theory.
 

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