Hydrazine hydrate (1:1) → 3-(4-ethylphenylmethyl)-5-methyl-1H-pyrazole

HRID 1625856Notes

Reaction equation

HRID 1625856 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=O)[CH:11]=[C:12](O)[CH3:13])=[CH:5][CH:4]=1)[CH3:2].O.[NH2:17][NH2:18]>C1(C)C=CC=CC=1>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]2[CH:11]=[C:12]([CH3:13])[NH:18][N:17]=2)=[CH:5][CH:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178436306HCID 178436306, compound

Product 1

HCID 666084723-(4-ethylphenylmethyl)-5-methyl-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of the above 1-(4-ethylphenyl)-4-hydroxy-3-penten-2-one (3.98 g) and hydrazine hydrate (4.0 ml) in toluene (20 ml) was stirred under heating at 100° C. for 1.5 hours. The reaction mixture was cooled to room temperature, and washed successively with water and brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:ethyl acetate=2:1) to give 3-(4-ethylphenylmethyl)-5-methyl-1H-pyrazole (3.12 g) as yellow oil. APCI-Mass m/Z 201 (M+H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed successively with water and brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-22b005cbb8f94316a33515d2f9954f9a
Source dataset
uspto-grants-2014_07
Patent number
US08785403B2

Reaction notes

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