Hydrochloric Acid → Ethyl 5-Chloro-1-methyl-1H-pyrazole-4-carboxylate

HRID 1731269Notes

Reaction equation

HRID 1731269 reaction equation
[ClH:1].N[C:3]1[N:7]([CH3:8])[N:6]=[CH:5][C:4]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10]>C(Cl)(Cl)Cl>[Cl:1][C:3]1[N:7]([CH3:8])[N:6]=[CH:5][C:4]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 271299Ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate

Product 1

HCID 2758821Ethyl 5-Chloro-1-methyl-1H-pyrazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

For a period of 60 minutes, hydrogen chloride gas was bubbled into a solution of 5-amino-1-methyl-1H-pyrazole-4-carboxylic acid, ethyl ester (12 grams, 0.07 mole) in 75 ml. of chloroform. The reaction mixture set up and nitrosyl chloride was bubbled into the reaction mixture for a period of five minutes. TLC indicated that starting material was still present, therefore, nitrosyl chloride was bubbled into the reaction mixture for an additional five minutes. The solution was heated on a steam bath for five minutes, then cooled and the solvent removed in vacuo, yielding 5-chloro-1-methyl-1H-pyrazole-4-carboxylic acid, ethyl ester. The identity of the product was confirmed by NMR.

Workup

  1. customnitrosyl chloride was bubbled into the reaction mixture for a period of five minutes
  2. customnitrosyl chloride was bubbled into the reaction mixture for an additional five minutes
  3. temperatureThe solution was heated on a steam bath for five minutes
  4. temperaturecooled
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-a89f8e54ac1a4d06abe1713c910e8f52
Source dataset
uspto-grants-1986_11
Patent number
US04620865

Reaction notes

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