Pentanenitrile, 4,4-dimethyl-3-oxo- → 4-(5-Amino-3-tert-butyl-1H-pyrazol-1-yl)benzonitrile

HRID 220222Notes

Reaction equation

HRID 220222 reaction equation
Cl.[NH:2]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1)[NH2:3].[CH3:12][C:13]([CH3:20])([CH3:19])[C:14](=O)[CH2:15][C:16]#[N:17]>CO>[NH2:17][C:16]1[N:2]([C:4]2[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=2)[N:3]=[C:14]([C:13]([CH3:20])([CH3:19])[CH3:12])[CH:15]=1

Participants

4

Reactant 2

HCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 162129624-Cyanophenylhydrazine Hydrochloride

Product 1

HCID 71470834-(5-Amino-3-tert-butyl-1H-pyrazol-1-yl)benzonitrileYield 82.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A flask was charged with 4-hydrazinylbenzonitrile hydrochloride (0.70 g, 3.8 mmol.), 4,4-dimethyl-3-oxopentanenitrile (0.48 g, 3.8 mmol) and MeOH and the reaction was heated at refluxed overnight. The reaction was cooled, and the solids which formed upon cooling were filtered off and discarded. Additional solids formed upon further standing (product) along with product material in solution. The solution containing, the solids was concentrated to yield 0.75 g of solid product (92%). MS M+1 (241).

Workup

  1. temperaturethe reaction was heated
  2. temperatureat refluxed overnight
  3. temperatureThe reaction was cooled
  4. customthe solids which formed
  5. temperatureupon cooling
  6. filtrationwere filtered off
  7. customAdditional solids formed upon further standing (product) along with product material in solution
  8. additionThe solution containing
  9. concentrationthe solids was concentrated

Sources & evidence

ORD record
ord-47f23733431e4f64928cf6f1025ffbcb
Source dataset
uspto-grants-2012_06
Patent number
US08202899B2

Reaction notes

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