Phenylhydrazine hydrochloride → 3-(1-Methylethyl)-1-phenyl-1H-pyrazol-5-amine

HRID 871719Notes

Reaction equation

HRID 871719 reaction equation
[CH3:1][CH:2]([CH3:8])[C:3](=O)[CH2:4][C:5]#[N:6].Cl.[C:10]1([NH:16][NH2:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CCO>[CH:2]([C:3]1[CH:4]=[C:5]([NH2:6])[N:16]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:17]=1)([CH3:8])[CH3:1]

Participants

4

Reactant 2

HCID 60962Phenylhydrazine hydrochlorideHCID 101299214-Methyl-3-oxopentanenitrile

Product 1

HCID 27595063-(1-Methylethyl)-1-phenyl-1H-pyrazol-5-amineYield 77.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

Using the procedure described in Example 308A Step 1, to a solution of 4-methyl-3-oxopentanenitrile (303 mg, 2.7 mmol) prepared as described in Example 122A Step 1, in anhydrous EtOH (6 ml) was added phenylhydrazine hydrochloride (473 mg, 3.3 mmol) and the reaction mixture was heated at 65° C. overnight. The residue was purified by silica gel chromatography (hexane/ethyl acetate 2-50%) to afford 3-isopropyl-1-phenyl-1H-pyrazol-5-amine (423 mg, 77%) as a solid. 1H NMR (300 MHz, CDCl3) δ 1.22 (d, J=6 Hz, 6H), 3.86 (brs, 2H), 5.35 (s, 1H), 7.21-7.49 (m, 5H); LC-MS (ESI) m/z 202 (M+H)+.

Workup

  1. customprepared
  2. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate 2-50%)

Sources & evidence

ORD record
ord-3dec57124ec849eb8ac0273bee908dd6
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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