Hydrazine → 1H-Indazole

HRID 459738Notes

Reaction equation

HRID 459738 reaction equation
FC[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[NH2:11][NH2:12]>C(O)CO>[NH:11]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:3]=[N:12]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 99472-Fluoro-1-phenylethan-1-one

Product 1

HCID 92211H-Indazole

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

100 g of fluoro-acetophenone in 400 mL of ethylene glycol was stirred at room temperature with hydrazine (0.624 mol, 20 g) for 4 h after which the reaction mixture was heated to 150 C for 48 h. TLC analysis indicated complete reaction. Partitioned the reaction mixture into dichloromethane and brine. Dried organic phase over sodium sulphate and evaporated to a solid. Re-crystallized from hexane/dicholomethane gave indazole.

Workup

  1. temperaturewas heated to 150 C for 48 h
  2. customreaction
  3. customPartitioned the reaction mixture into dichloromethane and brine
  4. customDried organic phase over sodium sulphate and evaporated to a solid

Sources & evidence

ORD record
ord-24a866c4b47c4c32ac49517504d51d3c
Source dataset
uspto-grants-2007_03
Patent number
US07196082B2

Reaction notes

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