Hydrazine hydrate (1:1) → HCID 178497263, compound

HRID 1178144Notes

Reaction equation

HRID 1178144 reaction equation
[NH2:1][NH2:2].O.[CH2:4]([O:6][C:7](=[O:19])[C:8](=O)[CH2:9][C:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)C>CO>[CH3:4][O:6][C:7]([C:8]1[CH:9]=[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[NH:2][N:1]=1)=[O:19]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 2265032,4-Dioxo-4-phenyl-butyric acid ethyl ester

Product 1

HCID 178497263HCID 178497263, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NH2—NH2—H2O (1.0 g, 20 mmol) was added to a solution of 2,4-dioxo-4-phenyl-butyric acid ethyl ester (1.94 g, 8.81 mmol) in methanol (17 mL). The resulting reaction mixture was heated to reflux for two and half hours. The methanol was evaporated and the resulting solid was heated with 2.5% ethyl acetate in hexane to afford 5-phenyl-1H-pyrazole-3-carboxylic acid methyl ester as a solid in 77.3% yield. LC-MS purity: 93.345%.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureto reflux for two and half hours
  4. customThe methanol was evaporated
  5. temperaturethe resulting solid was heated with 2.5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-249678e1f54b485bb3589580bf01fba9
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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