Hydrochloric Acid → 2-(5-amino-1-phenyl-1H-pyrazol-3-yl)-2-methylpropanenitrile

HRID 1930365Notes

Reaction equation

HRID 1930365 reaction equation
[CH3:1][C:2]([CH3:10])([C:5](=O)[CH2:6][C:7]#[N:8])[C:3]#[N:4].Cl.[C:12]1([NH:18][NH2:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl.C([O-])(O)=O.[Na+]>CCO>[NH2:8][C:7]1[N:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:19]=[C:5]([C:2]([CH3:10])([CH3:1])[C:3]#[N:4])[CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 60962Phenylhydrazine hydrochlorideHCID 516892Sodium BicarbonateHCID 866201652,2-Dimethyl-3-oxopentanedinitrile

Product 1

HCID 668758682-(5-amino-1-phenyl-1H-pyrazol-3-yl)-2-methylpropanenitrileYield 53.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2,2-dimethyl-3-oxopentanedinitrile (4.0 g, 29 mmol) and phenyl-hydrazine HCl salt (4.6 g, 31 mmol) in EtOH (50 mL) was treated with 2 N HCl solution (10 mL, 20 mmol). The reaction mixture was heated at reflux for 4 h. After cooling down, the mixture was neutralized with NaHCO3 to pH 7-8 and then extracted with EtOAc (3×100 mL). The organics were concentrated and the residue was purified by chromatography to give 2-(5-amino-1-phenyl-1 H-pyrazol-3-yl)-2-methylpropanenitrile (3.5 g, 33% yield, 2 steps). 1HNMR (300 MHz, DMSO-d6): δ 7.56-7.31 (m, 5 H), 5.52 (s, 1 H), 5.45 (br s, 2 H), 1.61 (s, 6 H); MS (ESI) m/z: 227.1(M+H+).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 4 h
  3. temperatureAfter cooling down
  4. extractionextracted with EtOAc (3×100 mL)
  5. concentrationThe organics were concentrated
  6. customthe residue was purified by chromatography

Sources & evidence

ORD record
ord-ee4b1836e8ec4e67a268af6cd9ba2443
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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