Acetic Acid → 3,5-Dimethyl-1-(alpha,alpha,alpha-trifluoro-m-tolyl)-pyrazol-4-acetic acid ethyl ester

HRID 2285956Notes

Reaction equation

HRID 2285956 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][CH:6]([C:10](=O)[CH3:11])[C:7](=O)[CH3:8])[CH3:2].[F:14][C:15]([F:25])([F:24])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][NH2:23])[CH:17]=1.C(O)(=O)C>C(O)C>[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[C:10]([CH3:11])=[N:23][N:22]([C:18]2[CH:17]=[C:16]([C:15]([F:14])([F:25])[F:24])[CH:21]=[CH:20][CH:19]=2)[C:7]=1[CH3:8])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 87820Ethyl 3-acetyl-4-oxopentanoateHCID 98650(3-(Trifluoromethyl)phenyl)hydrazine

Product 1

HCID 705469613,5-Dimethyl-1-(alpha,alpha,alpha-trifluoro-m-tolyl)-pyrazol-4-acetic acid ethyl esterYield 85.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

14.9 grams 3,3-diacetyl-propionic acid-ethyl ester, 14.1 grams (α,α,α-trifluoro-m-tolyl)-hydrazine, 4.8 grams glacial acetic acid and 100 milliliters ethanol were mixed, and the mixture heated to boiling temperature under reflux for 1 hour. The reaction mixture was evaporated and the residue distilled to produce 22.3 grams of crude 3,5-dimethyl-1-(α,α,α-trifluoro-m-tolyl)-pyrazol-4-acetic acid ethyl ester. This ester was saponified aas and worked up in accordance with the method described in Example (1b), using 4.0 grams sodium hydroxide as the base. The free acid was precipitated from the alkaline solution obtained in this manner by the addition of 2% acetic acid and of sufficient aqueous hydrochloric acid to complete the precipitation.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 1 hour
  3. customThe reaction mixture was evaporated
  4. distillationthe residue distilled

Sources & evidence

ORD record
ord-1c97d3a5cf084fcf865f848323787a81
Source dataset
uspto-grants-1982_04
Patent number
US04325962

Reaction notes

Loading…