Hydrochloric Acid → HCID 58851616, compound

HRID 1696430Notes

Reaction equation

HRID 1696430 reaction equation
[NH:1]([C:3]1[CH:4]=[C:5]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:6]=[CH:7][CH:8]=1)[NH2:2].[CH3:15][C:16]([CH3:23])([CH3:22])[C:17](=O)[CH2:18][C:19]#[N:20].Cl>CCO>[NH2:20][C:19]1[N:1]([C:3]2[CH:4]=[C:5]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:6]=[CH:7][CH:8]=2)[N:2]=[C:17]([C:16]([CH3:23])([CH3:22])[CH3:15])[CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 578094Acetic acid, 2-(3-hydrazinophenyl)-, ethyl ester

Product 1

HCID 58851616HCID 58851616, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl (3-hydrazinophenyl)acetate (15 g, 65 mmol) and 4,4-dimethyl-3-oxopentanenitrile (12.5 g, 0.1 mol) in EtOH (100 mL) containing conc. HCl (25 mL) was heated at reflux overnight. After removal of the solvent, the residue was washed with Et2O to afford ethyl 2-(3-(5-amino-3-t-butyl-1H-pyrazol-1-yl)phenyl)acetate (18 g). MS (ESI) m/z: 302 (M+H+).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customAfter removal of the solvent
  4. washthe residue was washed with Et2O

Sources & evidence

ORD record
ord-e580d72c24324adc8347a7ce41bf83c6
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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