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

HRID 1772181Notes

Reaction equation

HRID 1772181 reaction equation
[CH3:1][CH:2]([CH3:9])[C:3](=C=O)[CH2:4][C:5]#[N:6].[CH3:10][NH:11][NH2:12]>>[CH3:10][N:11]1[C:5]([NH2:6])=[CH:4][C:3]([CH:2]([CH3:1])[CH3:9])=[N:12]1

Participants

3

Reactant 2

HCID 6061MethylhydrazineHCID 866857984-Methyl-3-carbonyl valeronitrile

Product 1

HCID 27594993-Isopropyl-1-methyl-1H-pyrazol-5-amineYield 51.9%

Procedure

Under nitrogen atmosphere, the compound of Example 2A (8.03 g, 72 mmol) was dissolved in alcohol (50 mL). Methylhydrazine (3.32 g, 72 mmol) was added. The resultant mixture was slowly warmed and refluxed with stirring. The reaction was kept for 3 hr. The reaction was stopped and cooled to room temperature. Alcohol was rotary-evaporated to obtain a crude product as oil. The crude product was purified with column chromatography (eluant: petroleum ether/ethyl acetate=1:1) to give 5.2 g of the title compound. MS (ESI): m/z 140 (M+H)+

Workup

  1. temperaturerefluxed
  2. customAlcohol was rotary-evaporated
  3. customto obtain a crude product as oil
  4. customThe crude product was purified with column chromatography (eluant: petroleum ether/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-b0a427dbb42b4f299a59db135276713d
Source dataset
uspto-grants-2016_02
Patent number
US09249172B2

Reaction notes

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