Water → HCID 13654083, compound

HRID 1249436Notes

Reaction equation

HRID 1249436 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].C(O[CH:17]=[C:18]([C:24]#[N:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20])C.O>C(O)(=O)C>[NH2:25][C:24]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:17][C:18]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

5

Reactant 3

HCID 962WaterHCID 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 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 31.58 g of 2-(trifluoromethyl)-4-chlorophenylhydrazine and 27.92 g of ethyl (ethoxymethylene)cyanoacetate dissolved in 225 ml 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 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. customThe precipitated solid was collected by filtrate

Sources & evidence

ORD record
ord-e4f53441b38c485a91d1e1f961a9c12b
Source dataset
uspto-grants-1986_12
Patent number
US04631343

Reaction notes

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