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

HRID 1790324Notes

Reaction equation

HRID 1790324 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-52f9731d22ea41209e8550b5e70cad66
Source dataset
uspto-grants-2006_07
Patent number
US07071198B1

Reaction notes

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