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

HRID 1060920Notes

Reaction equation

HRID 1060920 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-0776eda0f3c7407aa7c023386215e1b9
Source dataset
uspto-grants-2003_02
Patent number
US06525059B1

Reaction notes

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