4-Methoxyphenylhydrazine hydrochloride → 3-isopropyl-1-(4-methoxyphenyl)-1H-pyrazol-5-amine

HRID 871746Notes

Reaction equation

HRID 871746 reaction equation
[CH3:1][CH:2]([CH3:8])[C:3](=O)[CH2:4][C:5]#[N:6].Cl.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][NH2:19])=[CH:14][CH:13]=1>CCO>[CH:2]([C:3]1[CH:4]=[C:5]([NH2:6])[N:18]([C:15]2[CH:16]=[CH:17][C:12]([O:11][CH3:10])=[CH:13][CH:14]=2)[N:19]=1)([CH3:8])[CH3:1]

Participants

4

Reactant 2

HCID 27239044-Methoxyphenylhydrazine hydrochlorideHCID 101299214-Methyl-3-oxopentanenitrile

Product 1

HCID 551588043-isopropyl-1-(4-methoxyphenyl)-1H-pyrazol-5-amineYield 48%

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-methyl-3-oxopentanenitrile (514 mg, 4.5 mmol) prepared as described in Example 122A Step 1, in anhydrous EtOH (15 ml) was added (4-methoxyphenyl)hydrazine hydrochloride (524 mg, 3.0 mmol) and the reaction mixture was heated at 80° C. overnight. The residue was purified by silica gel chromatography (DCM/EtOAc 1:1) to afford 3-isopropyl-1-(4-methoxyphenyl)-1H-pyrazol-5-amine (333 mg, 48%) as a solid. 1H NMR (300 MHz, CDCl3) δ 1.26 (d, J=7 Hz, 6H), 2.92 (m, 1H), 3.66 (s, 2H), 3.83 (s, 3H), 5.46 (s, 1H), 6.96 (d, J=9 Hz, 2H), 7.44 (d, J=9 Hz, 2H); LC-MS (ESI) m/z 232 (M+H)+.

Workup

  1. customprepared
  2. customThe residue was purified by silica gel chromatography (DCM/EtOAc 1:1)

Sources & evidence

ORD record
ord-5aa4eb6ea35d4d74bed7313f8fc693f4
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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