Chlorosuccinimide → 3-Chloro-1H-indazole-5-carboxaldehyde

HRID 1038397Notes

Reaction equation

HRID 1038397 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]=[O:11])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[Cl:12]N1C(=O)CCC1=O>C(#N)C>[Cl:12][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([CH:10]=[O:11])[CH:5]=2)[NH:1][N:2]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 212506441H-Indazole-5-carboxaldehyde2×

Product 1

HCID 1785193763-Chloro-1H-indazole-5-carboxaldehydeYield 97%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4.0 g (27.4 mmol) 1H-indazole-5-carbaldehyde [preparation described in US 2005/0227968-A1 (Intermediate 1)] in acetonitrile (116 ml) were added 4.2 g (31.5 mmol) N-chlorosuccinimide at room temperature. The resulting solution was stirred under reflux for 12 h. The mixture was then concentrated under reduced pressure yielding a solid precipitate. This material was triturated with water, filtered, and dried under high vacuum for 12 h to give the title compound (4.8 g, 97% of th.) as a white solid.

Workup

  1. temperatureunder reflux for 12 h
  2. concentrationThe mixture was then concentrated under reduced pressure
  3. customyielding a solid precipitate
  4. customThis material was triturated with water
  5. filtrationfiltered
  6. customdried under high vacuum for 12 h

Sources & evidence

ORD record
ord-c4a4464329f84edd961faf658f883487
Source dataset
uspto-grants-2013_10
Patent number
US08551989B2

Reaction notes

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