Methylhydrazine → 3-cyclopropyl-1-methyl-1H-pyrazol-5-amine

HRID 1478068Notes

Reaction equation

HRID 1478068 reaction equation
[CH:1]1([C:4](=O)[CH2:5][C:6]#[N:7])[CH2:3][CH2:2]1.[CH3:9][NH:10][NH2:11]>CC(O)=O>[CH:1]1([C:4]2[CH:5]=[C:6]([NH2:7])[N:10]([CH3:9])[N:11]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 98127633-Cyclopropyl-3-oxopropanenitrile

Product 1

HCID 27353113-cyclopropyl-1-methyl-1H-pyrazol-5-amineYield 100.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-cyclopropyl-3-oxo-propanenitrile (2.22 g, 20.3 mmol) in HOAc (40 mL) was added methylhydrazine (40% [w/w] in water, 2.81 g, 24.4 mmol). The reaction mixture was stirred at 100° C. overnight and then concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM) to give the title compound as yellow oil (2.80 g, 100%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by silica gel column chromatography (DCM)

Sources & evidence

ORD record
ord-03fc07e19c2344a88b163164258a4f70
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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