Hydrazine → HCID 178509224, compound

HRID 446909Notes

Reaction equation

HRID 446909 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]#[N:10])[C:5](Cl)=[N:6][CH:7]=1.[NH2:11][NH2:12]>C(O)CCC>[Br:1][C:2]1[CH:3]=[C:4]2[C:9]([NH2:10])=[N:12][NH:11][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 219482695-Bromo-2-chloronicotinonitrile

Product 1

HCID 178509224HCID 178509224, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

(Step 7-i) To a solution of 5-bromo-2-chloropyridine-3-carbonitrile (2 g, 9.22 mmol) in 30 mL n-butanol was added 2 mL anhydrous hydrazine. The reaction mixture was heated under reflux for 14 hrs and allowed to cool to room temperature. The solvent was removed by evaporation and the residue was poured into a saturated NaHCO3 solution. The resulting precipitate was collected and washed with water. After drying in vacuo, the product, 5-bromo-1H-pyrazolo[3,4-b]pyridin-3-amine, can be used directly without further purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 14 hrs
  3. customThe solvent was removed by evaporation
  4. additionthe residue was poured into a saturated NaHCO3 solution
  5. customThe resulting precipitate was collected
  6. washwashed with water
  7. customAfter drying in vacuo
  8. customthe product, 5-bromo-1H-pyrazolo[3,4-b]pyridin-3-amine, can be used directly without further purification

Sources & evidence

ORD record
ord-711450a1f81645fea6423bbc0b429397
Source dataset
uspto-grants-2013_07
Patent number
US08481538B2

Reaction notes

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