Sulfuric Acid → HCID 178481951, compound

HRID 1722459Notes

Reaction equation

HRID 1722459 reaction equation
[F:1]C(F)(F)C1NN=C(O)C=1.[F:11][C:12]([F:22])(F)[C:13](=O)[CH2:14][C:15](OCC)=[O:16].[CH3:23][NH:24][NH2:25].OC1NNC(=O)C1.S(=O)(=O)(O)O>CCOCC.C(Cl)(Cl)Cl>[CH3:23][N:24]1[C:13]([CH:12]([F:22])[F:11])=[C:14]([F:1])[C:15]([OH:16])=[N:25]1

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 6061MethylhydrazineHCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 19779905HCID 19779905, compound2×HCID 178516149HCID 178516149, compound

Product 1

HCID 178481951HCID 178481951, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Procedure

Another method of making 5-trifluoromethyl-3-hydroxypyrazole involves reacting the ethyl 4,4,4-trifluoroacetoacetate directly with the methylhydrazine in ether to form a mixture of the intermediates 5-hydroxypyrazolidin-3-one and 3-hydroxypyrazolidin-5-one and dehydration of these intermediates by the addition of sulfuric acid in chloroform to form a mixture of the 3- and 5-hydoxypyrazoles. The desired isomer can be separated as described above. Alternatively, 2,4,4 trifluoroacetoacetate can be reacted in a like manner to give 1-methyl-3-hydroxy-4-fluoro-5-difluoromethylpyrazole.

Workup

  1. customto form
  2. customto form
  3. customThe desired isomer can be separated
  4. customAlternatively, 2,4,4 trifluoroacetoacetate can be reacted in a like manner

Sources & evidence

ORD record
ord-f969f7d916a0457b93d75b0beb8cff60
Source dataset
uspto-grants-1989_08
Patent number
US04855442

Reaction notes

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