Hydrazine hydrate (1:1) → 6-bromo-1H-indazol-3-amine

HRID 2110273Notes

Reaction equation

HRID 2110273 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4](F)[CH:3]=1.O.[NH2:12][NH2:13]>C(O)C.O>[Br:1][C:2]1[CH:9]=[C:8]2[C:5]([C:6]([NH2:7])=[N:12][NH:13]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 7360294-Bromo-2-fluorobenzonitrile

Product 1

HCID 27866316-bromo-1H-indazol-3-amine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 10 g of 4-bromo-2-fluorobenzonitrile in 300 mL of ethanol is admixed with 7.29 mL of hydrazine hydrate. The reaction mixture is stirred for 22 hours at reflux and then concentrated under reduced pressure. The residue obtained is stirred for 30 minutes in 200 mL of distilled water. The suspended solid is isolated by filtration, washed with water and treated with suction. After drying under vacuum, 10 g of 6-bromo-3-amino-1H-indazole are obtained, whose characteristics are as follows:

Workup

  1. temperatureat reflux
  2. concentrationconcentrated under reduced pressure
  3. customThe residue obtained
  4. customThe suspended solid is isolated by filtration
  5. washwashed with water
  6. additiontreated with suction
  7. dry with materialAfter drying under vacuum, 10 g of 6-bromo-3-amino-1H-indazole
  8. customare obtained

Sources & evidence

ORD record
ord-5da4358bb81b495fba43eb88c30c40db
Source dataset
uspto-grants-2009_04
Patent number
US07517902B2

Reaction notes

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