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

HRID 222636Notes

Reaction equation

HRID 222636 reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].O.[NH2:11][NH2:12]>C(O)CCC>[NH2:5][C:4]1[C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=2[NH:12][N:11]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 678552-Fluorobenzonitrile

Product 1

HCID 133991H-indazol-3-amineYield 44%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

2-Fluorobenzonitrile (605 mg, 5 mmol) and 85% aqueous hydrazine hydrate (352 mg, 6 mmol) were mixed with 1-butanol (3 mL). The mixture was heated at reflux with stirring for 5 h then cooled to room temperature. The resulting precipitate was collected by filtration and washed with dichloromethane and the filter cake was dried in vacuo to give 3-amino benzpyrazole (293 mg, 44%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with dichloromethane
  5. customthe filter cake was dried in vacuo

Sources & evidence

ORD record
ord-8b603d892ebc4b94a248c2ce494aaa35
Source dataset
uspto-grants-2012_06
Patent number
US08207334B2

Reaction notes

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