Methylhydrazine → HCID 69424588, compound

HRID 916703Notes

Reaction equation

HRID 916703 reaction equation
[CH3:1][NH:2][NH2:3].[F:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13](=O)[CH:14]([CH3:25])[C:15]([C:17]2[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=2)[C:20]#[N:21])=O)=[CH:7][CH:6]=1>CCO>[F:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13]2[N:2]([CH3:1])[N:3]=[C:15]([C:17]3[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=3)[C:20]#[N:21])[C:14]=2[CH3:25])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 69423121HCID 69423121, compound

Product 1

HCID 69424588HCID 69424588, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

EtOH (20 mL) and methyl hydrazine (162 μL, 3.05 mmol) were added to the product of Step 1 (630 mg, 2.04 mmol) and the mixture heated at reflux for 90 min. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica eluting with 40% EtOAc/iso-hexanes to yield first 3-{5-[2-(4-fluorophenyl)-ethyl]-1,4-dimethyl-1H-pyrazol-3-yl}-benzonitrile (213 mg, 33%) (byproduct) and then the desired 3-{3-[2-(4-fluorophenyl)-ethyl]-1,4-dimethyl-1H-pyrazol-5-yl}-benzonitrile (250 mg, 38%).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 90 min
  3. customThe solvent was removed under reduced pressure
  4. customthe residue purified by column chromatography on silica eluting with 40% EtOAc/iso-hexanes

Sources & evidence

ORD record
ord-8a3f5fc3960c4a1f9de34761fe01da74
Source dataset
uspto-grants-2007_09
Patent number
US07271191B2

Reaction notes

Loading…