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

HRID 861047Notes

Reaction equation

HRID 861047 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-e89d5d44e96f47559e4a2ad91fa65082
Source dataset
uspto-grants-2006_12
Patent number
US07153959B2

Reaction notes

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