Hydrazine → HCID 178434598, compound

HRID 1369391Notes

Reaction equation

HRID 1369391 reaction equation
[C:1]1([C:7]2(O[CH:11]2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[C:8](=O)[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:19][NH2:20]>C(O)C>[CH3:9][C:8]1[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:11]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[NH:20][N:19]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 22225582HCID 22225582, compound

Product 1

HCID 178434598HCID 178434598, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-phenyl-4-(4-pyridyl)-3,4-epoxy-2-butanone (step 2) (350 mg, 1.46 mmol) and anhydrous hydrazine (0.7 ml, 20 mmol) in ethanol (3 ml) was heated at reflux for 4 hours. The reaction was cooled, and the solvent was evaporated to dryness. The resulting residue was purified by chromatography (silica gel, 1:1 acetone/hexane) to give the desired product as a crystalline solid, which was recrystallized from ethyl acetate and hexane to give pure 4-(3-methyl-4-phenyl-1H-pyrazol-5-yl)pyridine (145 mg, 42%): m. p. 164-165° C. Anal. Calc'd for C15H13N3 (235.29): C, 76.57; H, 5.57; N, 17.86. Found: C, 76.49; H, 5.45; N, 17.70.

Workup

  1. temperatureat reflux for 4 hours
  2. temperatureThe reaction was cooled
  3. customthe solvent was evaporated to dryness
  4. customThe resulting residue was purified by chromatography (silica gel, 1:1 acetone/hexane)

Sources & evidence

ORD record
ord-163881da3dc94f2a98422df6fc217ca7
Source dataset
uspto-grants-2003_06
Patent number
US06579873B2

Reaction notes

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