Hydrazine → HCID 178434568, compound

HRID 1058007Notes

Reaction equation

HRID 1058007 reaction equation
[C:1]1([CH:7]2O[C:8]2([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[C:9](=O)[CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:19][NH2:20]>C(O)C>[CH3:10][C:9]1[C:8]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[NH:20][N:19]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 220376354-Phenyl-3-(4-pyridyl)-3,4-epoxy-2-butanone

Product 1

HCID 178434568HCID 178434568, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Using the procedure of Example A-1, step 3, a solution of 4-phenyl-3-(4-pyridyl)-3,4-epoxy-2-butanone (step 3) (250 mg, 1 mmol) in ethanol (15 ml) was treated with anhydrous hydrazine (50 mg, 1.5 mmol) and heated to reflux for 4 hours. The crude product was purified by chromatography (silica gel, 1:1 acetone/hexane). The product was recrystallized from ethyl acetate and hexane to give 4-(3-methyl-5-phenyl-1H-pyrazol-4-yl)pyridine (81 mg, 35%) as a crystalline solid: m.p. 212-214° C. Anal. Calc'd for C15H13N3 (235.29): C, 76.57; H, 5.57; N, 17.86. Found: C, 76.49; H, 5.42; N, 17.39.

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 hours
  3. customThe crude product was purified by chromatography (silica gel, 1:1 acetone/hexane)
  4. customThe product was recrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-988496670b5f43abb9ef2d18b945241e
Source dataset
uspto-grants-2003_02
Patent number
US06514977B1

Reaction notes

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