Phenylhydrazine hydrochloride → 2-(5-amino-1-phenyl-1H-pyrazol-3-yl)-2-methylpropanenitrile

HRID 1918093Notes

Reaction equation

HRID 1918093 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>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

4

Reactant 2

HCID 60962Phenylhydrazine hydrochlorideHCID 866201652,2-Dimethyl-3-oxopentanedinitrile

Product 1

HCID 668758682-(5-amino-1-phenyl-1H-pyrazol-3-yl)-2-methylpropanenitrileYield 54%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2,2-dimethyl-3-oxopentanedinitrile (500 mg, 3.7 mmol) prepared as described in Example 125A Step 1, in anhydrous EtOH (33 ml) was added phenylhydrazine hydrochloride (763 mg, 3.7 mmol) and the reaction mixture was heated at 60° C. for 2 h. The solvent was removed under reduced pressure and the residue taken in EtOAc, washed with water and brine and the organics combined, dried (MgSO4) and concentrated. The residue was purified by silica gel chromatography (hexane/ethyl acetate 1:1) to afford 2-(5-amino-1-phenyl-1H-pyrazol-3-yl)-2-methylpropanenitrile (451 mg, 54%) as a solid. 1H NMR (300 MHz, CDCl3) δ 1.76 (s, 6H), 3.84 (brs, 2H), 5.69 (s, 1H), 7.26-7.57 (m, 5H); LC-MS (ESI) m/z 227 (M+H)+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. washwashed with water and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-689da67f28dc4d0ea8e0dca566d4fc17
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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