Hydrazine → 1H-Pyrazolo(4,3-b)pyridine

HRID 218464

Reaction equation

HRID 218464 reaction equation
F[C:2]1[C:3]([CH:8]=O)=[N:4][CH:5]=[CH:6][CH:7]=1.[NH2:10][NH2:11]>O>[NH:10]1[C:2]2[C:3](=[N:4][CH:5]=[CH:6][CH:7]=2)[CH:8]=[N:11]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 113440173-Fluoro-2-pyridinecarboxaldehyde

Product 1

HCID 216436531H-Pyrazolo(4,3-b)pyridineYield 60.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-fluoro-2-pyridinecarboxaldehyde (4 g, 32 mmol) and hydrazine (20.5 g) was kept at 115° C. for 7 hr, then cooled to rt. The reaction mixture was diluted with water and extracted with EtOAc. The organic phases were combined, washed with brine, and dried. Concentration followed by flash chromatography afforded 1H-pyrazolo[4,3-b]pyridine (2.3 g, 60.4%).

Workup

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. customdried
  4. concentrationConcentration

Sources & evidence

ORD record
ord-2a2bc17e86064d979af9365c6fef2b04
Source dataset
uspto-grants-2012_06
Patent number
US08198456B2

Linked notes

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