Hydrochloric Acid → HCID 58851646, compound

HRID 1696598Notes

Reaction equation

HRID 1696598 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][NH2:12])[CH:6]=1)[CH3:2].O=[C:15]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:16][C:17]#[N:18].Cl>C(O)C>[NH2:18][C:17]1[N:11]([C:7]2[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=2)[C:4]([O:3][CH2:1][CH3:2])=[O:13])[N:12]=[C:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 64799BenzoylacetonitrileHCID 21701845Ethyl 3-hydrazinylbenzoate

Product 1

HCID 58851646HCID 58851646, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 3-hydrazinobenzoic acid ethyl ester (4.5 g, 25.0 mmol) and commercially available 3-oxo-3-phenylpropionitrile (5.5 g, 37.5 mmol) in ethanol (50 mL) was added conc. HCl (5 mL). The resulting mixture was heated to reflux for 3 h. After removal of the solvent, the residue was washed with Et2O to afford ethyl 3-(5-amino-3-phenyl-1H-pyrazol-1-yl)benzoate (7 g, 2% yield, 2 steps) which was used in the next reaction without further purification.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 3 h
  3. customAfter removal of the solvent
  4. washthe residue was washed with Et2O

Sources & evidence

ORD record
ord-f100ff04f0e1480fb721bfc83d9d8e91
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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