Hydrazine hydrate (1:1) → 6-chloro-1H-indazole

HRID 2203332Notes

Reaction equation

HRID 2203332 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4](F)[CH:3]=1.O.[NH2:12][NH2:13]>CC(N(C)C)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]([CH:6]=[N:12][NH:13]2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 27249084-Chloro-2-fluorobenzaldehyde

Product 1

HCID 4175246-chloro-1H-indazole

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A DMA (250 mL) solution containing 4-chloro-2-fluorobenzaldehyde (50 g, 315 mmol) and hydrazine monohydrate (230 mL, 4730 mmol) was stirred for 30 minutes at room temperature. The solution was then stirred at 100° C. for 17 hours. The reaction mixture, which was a thick white slurry, was cooled to room temperature. The solid was collected by filtration, washed with water and dried under vacuum to give the indicated product.

Workup

  1. stirringThe solution was then stirred at 100° C. for 17 hours
  2. temperaturewas cooled to room temperature
  3. filtrationThe solid was collected by filtration
  4. washwashed with water
  5. customdried under vacuum
  6. customto give the indicated product

Sources & evidence

ORD record
ord-73536b410921445492b1b02365a75363
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

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