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

HRID 2282512Notes

Reaction equation

HRID 2282512 reaction equation
Cl.[C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][NH2:11])=[CH:6][CH:5]=1)#[N:3].[CH3:12][C:13]([CH3:20])([CH3:19])[C:14](=O)[CH2:15][C:16]#[N:17]>CCO>[NH2:17][C:16]1[N:10]([C:7]2[CH:8]=[CH:9][C:4]([C:2]#[N:3])=[CH:5][CH:6]=2)[N:11]=[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 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A cream suspension of 4-cyanophenylhydrazine hydrochloride (1.70 g, 10.0 mmol) and 4,4-dimethyl-3-oxopentanenitrile (1.31 g, 10.5 mmol) in EtOH (25 mL) was stirred at reflux for 4 h, then at RT for 64 h, and again at reflux for 24 h. The solution was cooled to RT, concentrated in vacuo, and partitioned between water (50 mL) and EtOAc (75 mL). The organics were washed with brine (50 mL), dried (Na2SO4), filtered and concentrated in vacuo to leave an orange solid (2.28 g, 95%). LCMS (Method 3): Rt 3.45 min, m/z 241 [MH+].

Workup

  1. temperatureat reflux for 4 h
  2. temperatureagain at reflux for 24 h
  3. concentrationconcentrated in vacuo
  4. custompartitioned between water (50 mL) and EtOAc (75 mL)
  5. washThe organics were washed with brine (50 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7131eb1a39d64f7d99ff8e6a35bc6ee2
Source dataset
uspto-grants-2015_09
Patent number
US09139584B2

Reaction notes

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