Methylhydrazine → Ethyl 3-ethyl-1-methyl-1H-pyrazole-5-carboxylate

HRID 530822Notes

Reaction equation

HRID 530822 reaction equation
O=[C:2]([CH2:8][C:9](=O)[CH2:10][CH3:11])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:13][NH:14][NH2:15]>C1(C)C=CC=CC=1>[CH2:10]([C:9]1[CH:8]=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[N:14]([CH3:13])[N:15]=1)[CH3:11]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 61590Ethyl-2,4-dioxohexanoate

Product 1

HCID 15131401Ethyl 3-ethyl-1-methyl-1H-pyrazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of compound 2 (3.8 g, 22 mmol) in toluene (20 mL) was added methylhydrazine (1.8 g, 0.039 mol) cooled to −20° C. After completion of the reaction, the reaction liquid was washed with water and the solvent was removed by evaporation to obtain crude product, the crude product was purified by silica gel column chromatography (PE:EA=5:1) to give the desired product as a white oil.

Workup

  1. customAfter completion of the reaction
  2. customthe reaction liquid
  3. washwas washed with water
  4. customthe solvent was removed by evaporation
  5. customto obtain crude product
  6. customthe crude product was purified by silica gel column chromatography (PE:EA=5:1)

Sources & evidence

ORD record
ord-a0b8861d490347c1ab4ced16ff1cd818
Source dataset
uspto-grants-2016_05
Patent number
US09353104B2

Reaction notes

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