Hydrochloric Acid → HCID 58851549, compound

HRID 1696599Notes

Reaction equation

HRID 1696599 reaction equation
[NH:1]([C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[NH2:2].[CH3:14][CH:15]([CH3:21])[C:16](=O)[CH2:17][C:18]#[N:19].Cl>C(O)C>[NH2:19][C:18]1[N:1]([C:3]2[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=2)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[N:2]=[C:16]([CH:15]([CH3:21])[CH3:14])[CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 101299214-Methyl-3-oxopentanenitrileHCID 21701845Ethyl 3-hydrazinylbenzoate

Product 1

HCID 58851549HCID 58851549, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of ethyl 3-hydrazinobenzoate (from Example A81, 3 g, 16.6 mmol) and 4-methyl-3-oxopentanenitrile (2.7 g, 24.9 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-isopropyl-1H-pyrazol-1-yl)benzoate (4 g), 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-4e3c63b6045649f6ac8bf397d11bccfc
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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