Hydrazine hydrate (1:1) → 3-Amino-5-bromo-1H-indazole

HRID 1162146Notes

Reaction equation

HRID 1162146 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:9]=1)[C:7]#[N:8].O.[NH2:12][NH2:13]>O>[NH2:8][C:7]1[C:6]2[C:5](=[CH:4][CH:3]=[C:2]([Br:1])[CH:9]=2)[NH:13][N:12]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 27249005-Bromo-2-fluorobenzonitrile

Product 1

HCID 8179103-Amino-5-bromo-1H-indazoleYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-bromo-2-fluorobenzonitrile (5.00 g, 25 mmol) and hydrazine hydrate (10 mL) was heated at reflux for two hours and then it was allowed to stand at room temperature for two days. The reaction was treated with water (50 mL) and the solids were collected by filtration to give 3-Amino-5-bromo-indazole as a white solid (4.82 g, 91%): mp 165-175° C.; MS [M+H]+ 212, 214.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for two hours
  3. filtrationthe solids were collected by filtration

Sources & evidence

ORD record
ord-48f441ac35d34c3f877041965344fe1b
Source dataset
uspto-grants-2010_10
Patent number
US07820670B2

Reaction notes

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