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

HRID 871691Notes

Reaction equation

HRID 871691 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-c74c2172bb384267950c63222199f6d4
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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