Pyridine → 3,5-Dimethyl-1-(3-nitrophenyl)-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 8058

Reaction equation

HRID 8058 reaction equation
Cl.[N+:2]([C:5]1[CH:6]=[C:7]([NH:11][NH2:12])[CH:8]=[CH:9][CH:10]=1)([O-:4])=[O:3].[CH2:13]([O:15][C:16](=[O:24])[CH:17]([C:21](=O)[CH3:22])[C:18](=O)[CH3:19])[CH3:14].N1C=CC=CC=1>C(O)C>[CH2:13]([O:15][C:16]([C:17]1[C:18]([CH3:19])=[N:12][N:11]([C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([N+:2]([O-:4])=[O:3])[CH:6]=2)[C:21]=1[CH3:22])=[O:24])[CH3:14]

Participants

5

Reactant 3

HCID 1049PyridineHCID 79063Ethyl 2-acetylacetoacetateHCID 54642853-Nitrophenylhydrazinium(1+) chloride

Product 1

HCID 6569693,5-Dimethyl-1-(3-nitrophenyl)-1H-pyrazole-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Similar to Example 1, m-nitrophenylhydrazine hydrochloride (10 mmol, 1.9 g) and 2-acetyl-3-oxo-butyric acid ethyl ester (10 mmol, 1.7 g) were mixed in a 50% solution of pyridine in ethanol. A precipitate was formed in the reaction medium, and was collected by filtration. Analysis confirmed synthesis of the named product, m.p., 107.7° C.–109.2° C.

Workup

  1. customA precipitate was formed in the reaction medium
  2. filtrationwas collected by filtration
  3. customsynthesis of the named product
  4. customm.p., 107.7° C.–109.2° C.

Sources & evidence

ORD record
ord-429914abd99c47c1b147ebf79f741665
Source dataset
uspto-grants-2006_08
Patent number
US07087634B2

Linked notes

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