Hydrochloric Acid → 6-(5-Amino-3-t-butylpyrazol-1-yl)indan-1-one

HRID 1696495Notes

Reaction equation

HRID 1696495 reaction equation
[NH:1]([C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][C:9]2=[O:12])=[CH:5][CH:4]=1)[NH2:2].[CH3:13][C:14]([CH3:21])([CH3:20])[C:15](=O)[CH2:16][C:17]#[N:18].Cl>CCO>[NH2:18][C:17]1[N:1]([C:3]2[CH:11]=[C:10]3[C:6]([CH2:7][CH2:8][C:9]3=[O:12])=[CH:5][CH:4]=2)[N:2]=[C:15]([C:14]([CH3:21])([CH3:20])[CH3:13])[CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 552812116-Hydrazinoindan-1-one

Product 1

HCID 672718246-(5-Amino-3-t-butylpyrazol-1-yl)indan-1-oneYield 38.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the 6-hydrazinoindan-1-one (2.1 g, 14.3 mmol) and 4,4-dimethyl-3-oxo-pentanenitrile (2.15 g, 1.2 eq) in EtOH (50 mL) was added conc. HCl (5 mL). The resulting mixture was heated at reflux overnight. After removal of the solvent, the residue was washed with ether to afford 6-(5-amino-3-t-butylpyrazol-1-yl)indan-1-one (1.1 g, 38.5% yield), which was put to the next reaction without further purification. MS (ESI) m/z: 270 (M+H+).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux overnight
  3. customAfter removal of the solvent
  4. washthe residue was washed with ether

Sources & evidence

ORD record
ord-4c4c8027cd6f47b8923520d0efbf2f44
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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