2-Propenoic acid, 2-cyano-3-ethoxy-, ethyl ester → HCID 13654083, compound

HRID 280450Notes

Reaction equation

HRID 280450 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:4]=1[NH:10][NH2:11].[CH2:14]([O:16][C:17](=[O:25])[C:18](=[CH:21]OCC)[C:19]#[N:20])[CH3:15]>C(O)(=O)C.O>[NH2:20][C:19]1[N:10]([C:4]2[CH:5]=[CH:6][C:7]([Cl:9])=[CH:8][C:3]=2[C:2]([F:1])([F:12])[F:13])[N:11]=[CH:21][C:18]=1[C:17]([O:16][CH2:14][CH3:15])=[O:25]

Participants

5

Reactant 2

HCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl esterHCID 2778240[4-Chloro-2-(trifluoromethyl)phenyl]hydrazine

Product 1

HCID 13654083HCID 13654083, compoundYield 85.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 31.58 g of 2-(trifluoromethyl)-4-chlorophenylhydrazine and 27.92 g of ethyl(ethoxymethylene)cyanoacetate dissolved in 225 of acetic acid and 75 ml of water was heated on a steam bath for approximately 16 hours. The reaction mixture was cooled to room temperature and placed in the refrigerator. The precipitated solid was collected by filtration and combined with the solids isolated from the filtrate to provide 43 g of 5-amino-1-[2-(trifluoromethyl)-4-chlorophenyl]-1H-pyrazole-4-carboxylic acid, ethyl ester. MP=114°-116° C.

Workup

  1. temperaturewas heated on a steam bath for approximately 16 hours
  2. filtrationThe precipitated solid was collected by filtration
  3. customisolated from the filtrate

Sources & evidence

ORD record
ord-9726254e7b62442ab15a5e8aa42de1e7
Source dataset
uspto-grants-1986_05
Patent number
US04589905

Reaction notes

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