Hydrazine hydrate (1:1) → HCID 178478063, compound

HRID 1167524Notes

Reaction equation

HRID 1167524 reaction equation
[Br:1][C:2]1[CH:7]=[C:6](/[C:8](=[CH:18]/[N:19](C)C)/[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=2)=O)[CH:5]=[CH:4][N:3]=1.O.[NH2:23]N>C(O)C>[Br:1][C:2]1[CH:7]=[C:6]([C:8]2[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=3)=[N:23][NH:19][CH:18]=2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 22037592HCID 22037592, compound

Product 1

HCID 178478063HCID 178478063, compoundYield 31.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the product from step 2 (650 mg, 1.8 mmol) and hydrazine monohydrate (100 mg) in ethanol (10 ml) was refluxed for 24 hours. Solvent was evaporated and the residue was chromatographed on silica gel using mixtures of ethyl acetate and toluene as eluents to give 2-bromo-4-[3-(3-chlorophenyl)-1H-pyrazol-4-yl]pyridine (190 mg, 31%) as an oil: Anal. Calc'd for C14H9BrClN3: C, 50.25; H, 2.71; N, 12.56. Found: C, 50.10; H, 2.60; N, 12.40.

Workup

  1. customSolvent was evaporated
  2. customthe residue was chromatographed on silica gel using mixtures of ethyl acetate and toluene as eluents

Sources & evidence

ORD record
ord-fec0685025934b56a423c284bdc51b59
Source dataset
uspto-grants-2003_09
Patent number
US06617324B1

Reaction notes

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