Hydrazine hydrate (1:1) → 4-chloro-1H-pyrazolo[4,3-c]pyridine

HRID 2206239Notes

Reaction equation

HRID 2206239 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]=O)=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.O.[NH2:12][NH2:13]>COCCOC>[Cl:1][C:2]1[C:7]2[CH:8]=[N:12][NH:13][C:6]=2[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 150539852,4-Dichloropyridine-3-carbaldehyde

Product 1

HCID 468356374-chloro-1H-pyrazolo[4,3-c]pyridineYield 65.5%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 2,4-dichloropyridine-3-carbaldehyde (7.0 g) in DME (70 mL) was added hydrazine monohydrate (8.0 g) at room temperature. The reaction mixture was stirred overnight at 75° C., and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (4.0 g).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-7f68ff6a687a4beabe077440bd05a565
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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