Methylhydrazine → 3-(4-Chlorobenzyl)-1-methyl-1H-pyrazol-5-ylamine

HRID 1644644Notes

Reaction equation

HRID 1644644 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=O)[CH2:10][C:11]#[N:12])=[CH:4][CH:3]=1.[CH3:14][NH:15][NH2:16]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:10]=[C:11]([NH2:12])[N:15]([CH3:14])[N:16]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 509888474-(4-Chlorophenyl)-3-oxobutanenitrile

Product 1

HCID 575512163-(4-Chlorobenzyl)-1-methyl-1H-pyrazol-5-ylamineYield 84.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-(4-chloro-phenyl)-3-oxo-butyronitrile (200 mg, 1 mmol, 1.0 equiv) and N-methylhydrazine (153 mg, 3.32 mmol, 3.2 equiv) in 4 mL of ethanol was heated at 100° C. in a sealed tube. After 4 d, the reaction mixture was cooled to ambient temperature and concentrated in vacuo. The residue was purified via automated flash chromatography (40 g SiO2, gradient from hexanes to ethyl acetate) to afford the product as a yellow solid (188 mg, 80%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified

Sources & evidence

ORD record
ord-67ac229c9ad14026814c2765b1225413
Source dataset
uspto-grants-2012_02
Patent number
US08124610B2

Reaction notes

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