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

HRID 871727Notes

Reaction equation

HRID 871727 reaction equation
[CH3:1][C:2]([CH3:9])([CH3:8])[C:3](=O)[CH2:4][C:5]#[N:6].Cl.[C:11]([C:13]1[CH:18]=[CH:17][C:16]([NH:19][NH2:20])=[CH:15][CH:14]=1)#[N:12]>CCO>[NH2:6][C:5]1[N:19]([C:16]2[CH:17]=[CH:18][C:13]([C:11]#[N:12])=[CH:14][CH:15]=2)[N:20]=[C:3]([C:2]([CH3:9])([CH3:8])[CH3:1])[CH:4]=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 44.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Using the procedure described in Example 308A Step 1, to a solution of 4,4-dimethyl-3-oxopentanenitrile (1 g, 7.99 mmol) in anhydrous EtOH (55 ml) was added 4-cyanophenyl hydrazine hydrochloride (473 mg, 3.3 mmol) and the reaction mixture was heated at 80° C. overnight. The residue was purified by silica gel chromatography (DCM/EtOAc 40%) to afford 4-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)benzonitrile (350 mg, 18%) as a solid. 1H NMR (300 MHz, CDCl3) δ 1.3 (s, 9H), 3.75 (brs, 2H), 7.72 (d, J=8.7 Hz, 2H), 7.83 (d, J=8.7 Hz, 2H); LC-MS (ESI) m/z 241 (M+H)+.

Workup

  1. customThe residue was purified by silica gel chromatography (DCM/EtOAc 40%)

Sources & evidence

ORD record
ord-86d5079d17a549a4862b8099a10bb895
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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